Pesticidal phosphoroamido(di)thioates

ABSTRACT

This invention relates to phosphoroamidothioate and phosphoroamidodithioate compounds, to compositions thereof which are useful as pesticides, for example, as athropodicides (that is, insecticides and acaricides), nematocides, and fungicides, and to a method of controlling pests, such as insects, acarids, nematodes, and fungi. The compounds of the invention are effective against soil insects, especially the corn rootworm, when applied by soil application techniques and are also effective when applied to agricultural plants and other plants by foliar application techniques.

This application is a division of U.S. Ser. No. 391,072 filed June 22, 1982, now U.S. Pat. No. 4,544,553, which is a continuation-in-part application of U.S. Ser. No. 276,780 filed June 24, 1981, now abandoned.

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to novel phosphoroamidothioate and phosphoroamidodithioate compounds, to compositions thereof which are useful as pesticides, for example, as arthropodicides (that is, insecticides and acaricides), nematocides, and fungicides, and to a method of controlling pests, such as insects, acarids, nematodes, and fungi. The compounds are effective when applied by soil application techniques and by foliar application techniques.

2. Description of the Prior Art

Ollinger, U.S. Pat. No. 4,263,288, issued Apr. 21, 1981, discloses acaricidal, insecticidal, and nematocidal phosphoroamidothioates having the formula

    [(A--N═C(R)](N(R.sup.1)]P(═X)(R.sup.2)(SR.sup.3)

wherein

A is aryl,

R is hydrogen or alkyl,

R¹ is alkyl, cycloalkyl, alkenyl, alkynyl or aralkyl,

R² is alkylthio, aryloxy, or amino,

R³ is alkyl, and

X is O or S.

The several Magee patents, U.S. Pat. Nos. 3,716,600, 4,049,679 (and continuation-in-part thereof, 4,110,443), 3,914,417, 3,845,172, 3,885,032, and 3,825,634, disclose insecticidal phosphoroamidothioates and phosphoroamidodithioates and methods of killing insects therewith. Column 18, lines 1-8 of U.S. Pat. No. 3,716,600 discloses broadly that, in addition to foliar application of the insecticidal compounds, one or more of the compounds may be applied in other liquid or solid formulations to the insects, their environment or hosts, for example, directly to plants or soil so as to effect control of insects coming into contact therewith. The compounds have the formula

    (RY)(R.sup.1 S)P(═O)(N(R.sup.3)(C(═O)R.sup.2)

wherein R, R¹, R², and R³, respectively, broadly, are alkyl, alkenyl, alkynyl, and haloalkyl, and Y is O or S.

The abstract of Japanese Pat. No. 77012251 discloses N--acyl--O--alkyl--S--alkyl(alkoxy, alkylthio, alkenyl, phenyl, alkoxycarbonyl, cyano, carbamoyl)--phosphoroamidothioates having insecticidal activity and having the formula

    [(R.sup.2 C(O)--N(H)]P(═O)(OR.sup.1)(S(CH.sub.2).sub.n R.sup.3).

Osborne, U.S. Pat. No. 3,399,213, discloses parasiticidal and fungicidal acylphosphoroamidate compounds having the formulas

    (G)(G)P(═Z)[N(G"')--C(═O)--G"--C(═O)-[OG']

and

    (G)(G)P(50 Z)[N(O)--C(═O)--G"--O]

wherein G represents lower alkylamino, alkoxy, alkylthio, alkylphenyl, phenoxy, and substituted phenyl.

Braxton, Jr., et. al., U.S. Pat. No. 3,511,635, discloses herbicidal organophosphorous--nitrogen compounds having the formula

    (R.sup.1)P(═X.sup.1)(--XR.sup.2)(═N(CH.sub.2).sub.n)

wherein

R¹ and R² are alkyl, alkenyl, diaryl, alkaryl, or aralkyl groups;

X and X¹ are O, S, or Se; and

n is an integer from 2-9.

Kishino et. al., U.S. Pat. No. 3,760,043, disclose O--phenyl--S--alkyl--N--alkyl--phosphoroamidothioates which possess fungicidal, acaricidal, insecticidal, and nematocidal properties and have the formula

    Aryl--O--P(═O)(NHR.sup.1)(SR.sup.2).

Schroeder, U.S. Pat. No. 3,657,426, discloses a method of controlling nematodes and other parasitic worm life existing in the soil at some stage of its life cycle by applying to the pests to be controlled or to the soil in which they live an effective amount of an O,O--dialkyl O-(1,2-dihydro-2-keto-1,6-dialkyl-4-pyridyl)phosphorothionate having the formula ##STR1##

Although the prior art discloses phosphoroamidothioate and phosphoroamidodithioate compounds having pesticidal, including insecticidal, activity, there remains a need for pesticidal compounds having improved pesticidal efficacy, and diminished detrimental effects such as mammalian toxicity and environmental waste, especially against soil insects such as the corn rootworm.

The prior art, including the several Magee patents described above which constitute the closest art known, do not provide any specific teaching illustrative of the insecticidal activity of the compounds therein disclosed when applied in the soil to protect against soil organisms. It is well known to those skilled in the art that organophosphates having a high order of contact insecticidal efficacy when applied to aerial, or foliar, portions of plants offer relatively little economic value as plant protectants when applied, or introduced, into the soil environment of the plants. Organophosphates tend to be susceptible to rapid degradative processes in the soil due to the combination of such factors as the hydrolytic action of soil moisture, unfavorable soil pH conditions, both of the above being exacerbated by the presence of soil microflora and fauna capable of rendering the insecticidal compound inactive. Application of a pesticide to the soil in ordinary agricultural practice does not necessarily or usually coincide with the presence of susceptible life stages of the target pest. For example, the hatching of insect eggs may be either delayed or it may occur over an interval of several days to several or many weeks. Insect ova are not generally affected by organophosphate pesticides. Thus, pesticidal compounds having satisfactory residual activity, especially in the soil--pesticidal compounds that retain their pesticidal efficacy under atmosphere conditions over an interval of several days to several or many weeks--are required in order to assure satisfactory protection of plants against soil insects. Further, it is highly desirable that such pesticidal compounds having activity persistent over an interval of several days to several or many weeks elicit control over a diverse selection of soil organisms that are agricultural pests.

SUMMARY OF THE INVENTION

It is an object of the invention to provide compounds, and compositions thereof, which are effective as pesticides, for example, as arthropodicides (including insecticides and acaricides), as nematocides, and as fungicides when applied by soil application or by foliar application techniques, especially against soil insects, for example the corn rootworm, and to provide a method for controlling said pests.

These and other objects as will become apparent, achieved by the present invention which comprises ##STR2## wherein: R¹ is unsubstituted or substituted (C₁ -C₄)alkyl wherein the substituent can be from one to four of the same or different bromo, chloro or fluoro groups;

(C₃ -C₆)alkenyl;

(C₃ -C₆)alkynyl;

unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or

unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

R² is unsubstituted or substituted (C₂ -C₅)alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms or, when X and Y are both S, CH₃ ; or

(C₃ -C₆)alkenyl;

(C₃ -C₆)alkynyl;

(C₃ -C₆)cycloaliphatic or heterocycloaliphatic;

unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or

unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

R³ is hydrogen;

methyl;

trifluoromethyl;

carbo(C₁ -C₄)alkoxy; or

thiocarbo(C₁ -C₄)alkoxy;

R⁴ is hydrogen;

unsubstituted or substituted (C₁ -C₇)alkyl wherein the substituent can be one to three of the same or different carbo(C₁ -C₄)alkoxy, halo, alkoxy, benzoyl, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; unsubstituted or substituted (C₃ -C₄)alkenyl wherein the substituent can be from one to three of the same or different phenyl, alkyl, carbo(C₁ -C₄)alkoxy, bromo, chloro or fluoro groups;

(C₃ -C₆)alkynyl;

unsubstituted or substituted phenyl wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or

unsubstituted or substituted phenyl, or naphthyl, (C₁ -C₃)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, benzyloxy, methylenedioxy, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

X, Y and Z are independently O or S provided that both X and Y are not O at the same time except that, in the case that X and Y are both O and Z is S, then R¹ is n--C₃ H₇ or s--C₄ H₉, R² is s--C₄ H₉, R³ is H, and R⁴ is CH₃.

In another aspect, this invention comprises a pesticidal composition, especially an insecticidal composition comprising a pesticidally effective amount of the compound of the invention defined herein above.

In yet another aspect, this invention comprises a method of controlling pests, insects, nematodes, acarids, and fungi, especially soil insects and pests, which comprises applying to the pests, insects, nematodes, acarids and fungi comprising applying on or in the soil or to the loci of plants to be freed from infestation a pesticidally or insecticidally effective amount of an active compound having the formula (I) defined herein above, or of a compound of formula (I) above except that X, Y and Z are independently O or S wherein X and Y may both be O at the same time.

In the practice of the method of the invention, the active compound may be applied to the soil, absorbed by plants grown in the soil, and ultimately ingested by the pests, insects, nematodes, acarids or fungi by means of ingestion of the plant part(s). This means of application is referred to as "systemic" application. Alternatively, the active compound may be applied to the soil and contacted therein with the insects and other pests to be controlled. This means of application is referred to as "soil" application. In another alternative the active compound may be foliarly applied to the plants to be freed from insects and other pests.

When using the compounds defined above, the method of the invention is especially effective against soil insects when the active compound is applied on or in the soil in order to effect direct contact with the insects or other pests, including nematodes, acarids and fungi. By "pests" is meant organisms including arthropods, which in turn includes insects and acarids, nematodes, and fungi, which organisms attack agricultural plants.

In a preferred embodiment for soil application, this invention comprises a compound according to formula (I) wherein:

R¹ is unsubstituted or substituted (C₁ -C₄)alkyl wherein the substituent can be from one to three of the same or different bromo, chloro or fluoro groups;

unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or

unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

R² is unsubstituted or substituted (C₂ -C₅)alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

(C₃ -C₆)alkenyl;

(C₃ -C₆)cycloaliphatic or heterocycloaliphatic;

unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or

unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

R³ is hydrogen;

methyl; or

trifluoromethyl; and

R⁴ is hydrogen;

unsubstituted or substituted (C₁ -C₇)alkyl wherein the substituent can be one to three of the same or different carbo(C₁ -C₄)alkoxy, halo, alkoxy, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

(C₃ -C₆)alkenyl;

(C₃ -C₆)alkynyl;

unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent is on the phenyl lring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms.

In a more preferred embodiment for soil application, this invention comprises a compound according to formula (I) wherein:

R¹ is methyl, ethyl, 2,2,2-trifluoroethyl, phenyl or benzyl;

R² is unsubstituted straight or branched chain (C₃ -C₅)alkyl, phenyl or benzyl;

R³ is hydrogen, methyl, or trifluoromethyl; and

R⁴ is methyl, ethyl, n--propyl, propenyl or unsubstituted or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different (C₁ -C₃)alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro, or cyano groups.

In a most preferred embodiment for soil application, this invention comprises a compound according to formula (I) wherein:

R¹ is methyl, ethyl, or 2,2,2-trifluoroethyl;

R² is n--propyl, 3-pentyl, or 1-methylpropyl;

R³ is hydrogen;

R⁴ is methyl, ethyl, or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to two of the same or different (C₁ -C₃)alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro, or cyano groups;

X and Y are, independently, O or S; and

Z is O.

Especially preferred embodiments of this invention comprise compounds having the following formulas:

(H₅ C₂ O)P(S)(S sec--C₄ H₉)(N(C₂ H₅)(CHO));

(H₅ C₂ O)P(S)(S sec--C₄ H₉)(N(C₂ H₅)(CHS));

(H₅ C₂ O)P(S)(S sec--C₄ H₉)(N(CH₃)(CHO));

(H₅ C₂ O)P(O)(S sec--C₄ H₉)(N(C₂ H₅)(CHS)); and

(H₅ C₂ O)P(S)(S sec--C₄ H₉)(N(CH₂ C₆ H₄ CF₃ --3)(CHO)).

The development of the class of compounds described above led to the preparation of analogous compounds which were found to possess advantageous pesticidal efficacy when applied to agricultural plants by foliar application techniques. In a preferred embodiment for foliar application, the invention comprises a compound having the formula ##STR3## wherein: R¹ is unsubstituted or substituted (C₁ -C₄)alkyl wherein the substituent can be one (C₁ -C₄)alkoxy or from one to three of the same or different bromo, chloro or fluoro groups;

(C₃ -C₆)alkenyl;

(C₃ -C₆)alkynyl;

unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or

unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

R² is unsubstituted or substituted C₂ -C₅)alkyl wherein the substituent can be from one to three of the same of different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or

(C₃ -C₆)alkenyl;

(C₃ -C₆)alkynyl;

(C₃ -C₆)cycloaliphatic or heterocycloaliphatic;

unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or

unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

R³ is hydrogen;

R⁴ is substituted (C₁ -C₇)alkyl wherein the substituent can be one to three of the same or different phenylcarbonyl, carbo(C₁ -C₄)alkoxy, halo, alkoxy, benzoyl, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

unsubstituted or substituted (C₃ -C₆)alkenyl wherein the substituent can be from one to three of the same or different phenyl, carbo(C₁ -C₄)alkoxy, bromo, chloro or fluoro groups;

(C₃ -C₆)alkynyl;

unsubstituted or substituted phenyl, or naphthyl, (C₁ -C₃)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkyamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; and X, Y and Z are each O.

In a more preferred embodiment for foliar application, this invention comprises a compound according to formula (I) wherein

R¹ is unsubstituted or substituted (C₁ -C₄)alkyl wherein the substituent can be from one to three of the same or different bromo, chloro or fluoro groups;

unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or

unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

R² is unsubstituted or substituted (C₂ -C₅)alkyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

(C₃ -C₆)alkenyl;

(C₃ -C₆)cycloaliphatic or heterocycloaliphatic;

unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkythio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups; wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

R³ is hydrogen;

R⁴ is substituted (C₁ -C₇)alkyl wherein the substituent can be one to three of the same or different carbo(C₁ -C₄)alkoxy, halo, alkoxy, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, alkylthio, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

(C₃ -C₆)alkenyl;

(C₃ -C₆)alkynyl;

unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substitutent is on the phenyl ring and wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;

In a most preferred embodiment for foliar application, this invention comprises a compound according to formula (I) wherein

R¹ is methyl, ethyl, 2,2,2-trifluoromethyl, phenyl, or benzyl;

R² is unsubstituted straight or branched chain (C₃ -C₅)alkyl, phenyl, or benzyl;

R³ is hydrogen; and

R⁴ is unsubstituted or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to two of the same or different (C₁ -C₃)alkyl, fluoro, chloro, bromo, trifluoromethyl, nitro or cyano groups.

In an especially preferred embodiment for foliar application, this invention comprises a compound according to formula (I) wherein:

R¹ is methyl, ethyl, or 2,2,2-trifluoroethyl;

R² is n--propyl, 3-pentyl, or 1-methylpropyl;

R³ hydrogen; and

R⁴ is unsubstituted or substituted benzyl wherein the substituent can be from one to two (C₁ -C₃)alkyl, fluoro, chloro, bromo, trifluoromethyl, nitro or cyano groups.

Compounds illustrative of the invention include the following:

N-methyl-N-hydrogenthiocarbonyl-O-ethyl-S-n-butyl phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-n-butyl phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-n-butyl phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylpropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(2-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-pentyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-pentyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(1-pentyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(2-methylbutyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylbutyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylbutyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylbutyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylbutyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(1-methylbutyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-methylbutyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-methylbutyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(3-methylbutyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2,2-dimethylpropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2,2-dimethylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(2,2-dimethylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methoxyethyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methoxyethyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(2-methoxyethyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(3-nitropropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-nitro propyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-cyanoethyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-cyanoethyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(2-cyanoethyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(3-chloropropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-chloropropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-chloropropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(2-fluoroethyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-fluoroethyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-fluoroethyl)phosophoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-ethylthiomethyl phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-ethylthioethyl phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-ethylthiomethyl phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl]phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl]phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl]phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(2-bromoallyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-bromoallyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-bromoallyl)phosphoroamidothioate

N-methyl N-hydrogencarbonyl O-ethyl S-(3-butenyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-butenyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-butenyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-butenyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-butenyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(2-butenyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(5-hexenyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-hexenyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-hexenyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-propargyl phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-propargyl phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-propargyl phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-phenyl phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-phenyl phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-phenyl phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-trichlorophenyl phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-trichlorophenyl phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-trichlorophenyl phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-phenylethyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-phenylethyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(1-phenylethyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-ethyl S-(5-phenyl-1-pentyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-phenyl-1-pentyl)phosphoroamidodithioate

N-methyl N-methylcarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-butylcarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-heptyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-heptyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

N-heptyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(3-methoxypropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

N-(3-methoxypropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(3-methoxylpropyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(3-chloropropyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(3-chloropropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

N-(3-chloropropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(2-fluoroethyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

N-(2-fluoroethyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(2-butenyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(2-butenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

N-(2-butenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(5-hexenyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(5-hexenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(5-hexenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothiaote

N-[(2-carboethoxy)-1-propenyl]N-hydrogenthiocarbonyl O-ethyl S-(1 methylpropyl)phosphoroamidothioate

N-[(2-carboethoxy)-1-propenyl]N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-[(2-carboethoxy)-1-propenyl]N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(3-hexyn-1-yl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(3-hexyn-1-yl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(3-hexyn-1-yl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

N-phenyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-phenyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

N-phenyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-p-chlorobenzyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

N-p-chlorobenzyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-p-chlorobenzyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(5-phenyl-1-pentyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-(5-phenyl-1-pentyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

N-(5-phenyl-1-pentyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl-O-propyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-propyl S-(1-methylpropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-propyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-n-butyl S-(1-methylpropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-n-butyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-n-butyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-(2,2,2-trifluoroethyl)S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-(2,2,2-trifluoroethyl)S-(1-methylpropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-(2,2,2-trifluoroethyl)S-1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-allyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-allyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarobnyl O-allyl S-(1-methylpropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-(3-butenyl)S-(1-methylpropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarobnyl O-(3-butenyl)S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-(3-butenyl)S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-propargyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-propargyl S-(1-methylpropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-propargyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-(3-hexyn-1-yl)S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-(3-hexyn-1-yl)S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-phenyl S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-phenyl S-(1-methylpropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-pheny S-(1methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogencarbonyl O-(2-phenylethyl)S-(1-methylpropyl)phosphoroamidodithioate

N-methyl N-hydrogenthiocarbonyl O-(2-phenylethyl)S-(1-methylpropyl)phosphoroamidothioate

N-methyl N-hydrogenthiocarbonyl O-(2-phenylethyl S-(1-methylpropyl)phosphoroamidodithioate

S,S'-dibutyl N-hydrogenthiocarbonyl N-methyl phosphoroamidodithioate

N-hydrogencarbonyl N,S-dimethyl S'-(1-methylpropyl)phosphoroamidotrithioate

N-methylthiocarbonyl N,S,S'-tripropyl phosphoroamidodithioate

S-ethyl N-heptyl S'-propyl N-trifluoromethylcarbonyl phosphoroamidotrithioate

S-methyl S'-pentyl N-propyl N-propoxymethylthiocarbonyl phosphoroamidodithioate

S-ethyl S'-(2-hexenyl)N-methyl N-trifluoromethylthiocarbonyl phosphoroamidotrithioate

N-ethyl S-methyl S'-(2-propenyl)N-trifluoromethyl phosphoroamidotrithioate

N-ethyl N-hydrogenthiocarbonyl S-methyl S'-(1-methylpropyl)phosphoroamidodithioate

N-ethyl N-hydrogenthiocarbonyl S-(1-methylpropyl)S'-(2-propynyl)phosphoroamidotrithioate

N-ethyl S-(2-hexynyl)N-hydrogencarbonyl S'-(1-methylpropyl)phosphoroamidotrithioate

S-(2-fluorobutyl)N-hydrogenthiocarbonyl N-methyl S'-(1-methylethyl)phosphoroamidodithioate

N-methylcarbonyl S-phenyl N,S'-dipropyl phosphoroamidodtrithioate

S-benzyl S'-(1-ethylpropyl)N-hydrogenthiocarbonyl N-methyl phosphorotriamidothiate

S-butyl N-ethyl N-methylcarbonyl S'-(5-phenylpentyl)phosphoroamidotrithioate

S-butyl N-methylthiocarbonyl N-(2-propenyl)S'-propyl phosphoroamidodithioate

N-(3-hexenyl)N-hydrogencarbonyl S,S'-dipropyl phosphoroamidotrithioate

N-(3-hexynyl)N-hydrogenthiocarbonyl S-methyl S'-(1-methylpropyl)phosphoroamidodithioate

S-ethyl N,S'-di-(3-propynyl)N-trifluoromethylthiocarbonyl phosphoroamidodithioate

N-benzyl N-hydrogenthiocarbonyl S,S'-dipropyl phosphoroamidotrithioate

N-(carbomethoxymethyl)-N-hydrogencarbonyl O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

N-(carboethoxymethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-(cyanomethyl)-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidodithioate

N-(methoxymethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

N-(methylthiomethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-benzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

N-butyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

N-4-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-3-methoxybenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-3-trifluoromethylbenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-4-chlorophenylthiomethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-3-phenyl-2-butenyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidodithioate

N-1-methylbenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-4-nitrobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

N-4-cyanobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

N-phenyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidodithioate

N-4-chlorophenoxymethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-1-naphthylmethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-2-bromobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidodithioate

N-2-chloro-6-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-4-methylthiobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidodithioate

N-benzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

N-2-chloro-6-fluorobenzyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

N-3-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

N-2-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

N-3-cyanobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidothioate

N-3-nitrobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate

The method of controlling arthropods, including insects, nematodes, acarids, other pests, and fungi, according to the invention, comprises applying directly to the insects, nematodes, acarids, other pests and fungi or to the loci to be freed or protected from attack by the arthropods--insects, nematodes, acarids, other pests and fungi--an arthropodocidally effective amount of an active compound having the formula (I) defined hereinabove except that X, Y and Z are independently O or S.

In one preferred aspect, the method of the invention comprises applying on or in the soil an arthropodocidally or pesticidally or fungicidally effective amount of the active compound having the formula (I) above wherein:

R¹ is methyl, ethyl, 2,2,2-trifluoroethyl, phenyl or benzyl;

R² is unsubstituted straight or branched chain (C₃ -C₅)alkyl, phenyl or benzyl;

R³ is hydrogen;

R⁴ is methyl, ethyl, n--propyl, propenyl, or unsubstituted or substituted benzyl; and

X, Y and Z are, independently, O or S.

The following compounds are illustrative of the more preferred group of compounds useful by soil application techniques:

(H₅ C₂ O)P(O)(S--n--C₃ H₇)(N(C₂ H₅)(CHO));

(H₅ C₂ O)P(S)(S--sec--C₄ H₉)(N(C₂ H₅)(CHO));

(H₅ C₂ O)P(S)(S--sec--C₄ H₉)(N(C₂ H₅)(CHS));

(H₂ C₂ O)P(O)(S--n--C₃ H₇)(N(CH₃)(CHO));

(H₂ C₂ O)P(O)(S--n--C₃ H₇)(N(CH₃)(CHS));

(H₅ C₂ O)P(S) (S--n--C₃ H₇)(N(CH₃)(CHO));

(H₅ C₂ O)P(S)(S--n--C₃ H₇)(N(CH₃)(CHS))

(H₅ C₂ O)P(O)(S--sec--C₄ H₉)(N(CH₃)(CHS))

(H₅ C₂ O)P(S)(S--sec--C₄ H₉)(N(CH₂ CF₃)(CHO))

(H₅ C₂ O)P(S)(S--sec--C₄ H₉)(N(CH₂ CH═CH₂)(CHO)); and

(H₅ C₂ O)P(O)(S--3--pentyl)(N(C₂ H₅)(CHS)).

Especially preferred the method of the invention are the following compounds:

(H₅ C₂ O)P(S)(S--sec--C₄ H₉)(N(C₂ H₅)(CHO));

(H₅ C₂ O)P(S)(S--sec--C₄ H₉)(N(C₂ H₅)(CHS)); and

(H₅ C₂ O)P(S)(S--sec--C₄ H₉)(N(CH₃)(CHO)).

In another preferred aspect, the method of the invention comprises applying to agricultural plants for foliar application techniques, an arthropodically or pesticidally or fungicidally effective amount of the active compound having the formula (I) above wherein:

R¹ is methyl, ethyl, 2,2,2-trifluoromethyl, phenyl or benzyl;

R² is unsubsitutued straight or branched chain (C₃ -C₅)alkyl, phenyl, or benzyl;

R³ is hydrogen;

R⁴ is unsubstituted or substituted alkyl or unsubstituted or substituted benzyl; and

X, Y, and Z are each O.

The following compounds are illustrative of the more preferred groups of compounds useful by foliar application techniques:

(H₅ C₂ O)P(S)(S--sec--C₄ H₉)(N(CH₂ C₆ H₄ CN--4)(CHO))

(H₅ C₂ O)P(S)(S--sec--C₄ H₉ )(N(CH₂ C₆ H₄ F--4)(CHO))

Especially preferred n the foliar application method of the invention are the compounds:

(H₅ C₂ O)P(S)(S--sec--C₄ H₉)(N(CH₂ C₆ H₄ CN--4)(CHO))

(H₅ C₂ O)P(S)(S--sec--C₄ H₉)(N(CH₂ C₆ H₄ NO₂ --4)(CHO))

The compounds useful according to this invention can be obtained by several reaction sequences. One method for the preparation of hydrogencarbonyl and hydrogenthiocarbonyl phosphoroamido(di)thioates involves conversion of S-alkyl phosphorodichlorothioates to the products in four or five steps as is illustrated by the following reaction scheme: ##STR4##

Another method for the preparation of hydrogencarbonyl and hydrogenthiocarbonyl phosphoroamido(di)thioates involves the S-alkylation of suitably substituted salts according to the following reaction: ##STR5##

The product of this alkylation reaction having the formula (IV) can then be further treated as illustrated in the reaction scheme set forth above to obtain the new compounds of the invention having the formula (VIII) and (XI).

Still another method for the preparaton of hydrogencarbonyl and hydrogenthiocarbonyl phosphoroamido(di)thioates involves the reaction of diethyl chlorophosphite with a suitably substituted sulfenyl halide to obtain an intermediate O,S-disubstituted phosphorochloridothioate, corresponding to formula (III), designated below by the formula number (III'), in the reaction scheme set forth above, as follows: ##STR6##

Intermediate (III') can be further reacted as set forth in the reaction scheme illustrated above to obtain the desired end products.

Yet another method for the preparation of hydrogencarbonyl and hydrogenthiocarbonyl phosphoroamido(di)thioates involves the N-alkylation in the presence of a suitable base of a hydrogencarbonyl phosphoroamido(di)thioate according to the following reaction: ##STR7##

The product of this reaction having the formula (VI) can be further reacted as set forth in the reaction scheme illustrated above to obtain the hydrogenthiocarbonyl phosphoroamido(di)thioate compound having the formula (VIII).

The S,S-dialkyl phosphoroamidodithioates of the invention can be prepared according to the following sequence: ##STR8##

For use as pesticides, the compounds of this invention can be used as solutions, suspensions, or mixtures, in organic solvents or formulations. For example, they can be formulated as wettable powders, emulsifiable concentrates, dusts, granular formulations or flowable emulsifiable concentrates. In such formulations, the compounds of this invention are present at a concentration of about 0.00001 to about 99%, preferably about 1 to about 95%, and are extended with an agronomically acceptable liquid or solid carrier. When desired, suitable surfactants are likewise incorporated. Surfactants commonly used in the art can be found in the John W. McCutcheon, Inc. publication "Detergents and Emulsifiers Annual."

By "agronimically acceptable carrier" is meant any substance which can be utilized to dissolve, disperse or diffuse the chemical incorporated therein without impairing the effectiveness of the toxic agent and which does not create permanent damage to such environment as soil, equipment, and agronomic crops when utilized according to recommendations.

The compounds of this invention can be taken up on or mixed with a finely particled solid carrier, as for example, clays, inorganic silicates, carbonates, and silicas. Organic carriers can also be employed.

Dust concentrates are commonly made wherein compounds are present in the range of about 20 to 80%. For ultimate applications, these concentrates are normally extended with additional solid to given an active ingredient content of from 1 to about 20%. Granular formulations are being made using a granular or pelletized form of carrier, such as granular clays, vermiculite, charcoal or corn cobs, and may contain the active ingredient from about 1 to about 25% by weight.

Wettable powder formulations are made by incorporating the compounds of this invention in an inert, finely divided solid carrier along with a surfactant which can be one or more elulsifying, wetting, dispersing, or spreading agents or a blend of these. The compounds are usually present in the range of about 10 to about 80% by weight and surfactants in from about 0.5 to about 10% by weight. Commonly used emulsifying and wetting agents include polyoxyethylated derivatives of alkylphenols, fatty alcohols, fatty acids, alkylamines, alkylarene sulfonates and dialkyl sulfosuccinates. Spreading agents include such material as glycerol mannitan laurate and a condensate of polygylcerol and oleic acid modified with phthalic anhydride. Dispersing agents include such materials as the sodium salt of the copolymer of maleic anhydride and an olefin such as diisobutylene, sodium lignin sulfonate and sodium formaldehydenaphthalene sulfonates.

One convenient method for preparing a solid formulation is to impregnate the compounds of this invention onto the solid carrier by means of a volatile solvent, such as acetone. In this manner, adjuvants, such as activators, adhesives, plant nutrients, synergists and various surfactants can also be incorporated.

Emulsifiable concentrate formulations are prepared by dissolving the compounds of this invention in an agronomically acceptable organic solvent and adding a solvent-soluble emulsifying agent. Suitable solvents are usually water-immiscible and can be found in the hydrocarbon, chlorinated hydrocarbon, ketone, ester, alcohol and amide classes of organic solvents. Mixtures of solvents are commonly employed. The surfactants useful as emulsifying agents can constitute about 0.5 to about 10% by weight of emulsifiable concentrates and can be anionic, cationic or non-ionic in character. The concentration of the active ingredients can vary from about 10 to about 80%, preferably in the range of about 25 to about 50%.

For use as pesticidal agents, these compounds should be applied in an effective amount sufficient to exert the desired pesticidal activity by techniques well known in the art. In certain situations, however, it may be desirable and advantageous to apply the compounds directly onto the loci to be protected or freed of pests without the benefit of any substantial amount of carrier. This is a particularly effective method when the physical nature of the toxicants is such as to permit what is known as "low-volume" application, that is, when the compounds are in liquid form or substantially soluble in higher boiling solvents.

The application rate will, of course, vary depending upon the purpose of such application, the compound being utilized, the frequency of dissemination, and the like.

Many of the above formulations can be utilized on animals for the control of parasites.

For use as arthropodicides, e.g. acaricides and insecticides, dilute sprays can be applied at concentrations of about 0.01 to about 20 pounds of the active ingredients per 100 gallons of spray. They are usually applied at about 0.1 to about 5 pounds per 100 gallons. In more concentrated sprays, the active ingredient is increased by a factor of 2 to 40. With dilute sprays, applications are usually made to the plants until run-off is achieved, whereas with more concentrated or low-volume sprays, the materials are applied as mists.

For use as a nematocide or as a soil insecticide, the compounds can be applied as a dilute liquid preparation or as a solid formulation, preferably a granular formulation, by broadcasting, side-dressing, introduction into the seed furrow, soil incorporation, or seed treatment. The application rate can be from about 1 to about 50 pounds per acre of active ingredient and for economic reasons, preferably from about 1 to about 25 pounds per acre.

For use as a fungicide, the organophosphorothiolate or phosphorodithioate can be applied by methods commonly employed, such as conventional high-gallonage hydraulic sprays, low-gallonage sprays, air-blast sprays, aerial sprays and dusts. The dilution and rate of application will depend upon the type of equipment employed, the method of application and diseases to be controlled, but the preferred effective amount is usually about 0.1 to about 50 pounds per acre of the active ingredient.

As a fungicidal seed protectant, the amount of toxicant coated on the seed is usually at a dosage rate of about 0.1 to about 20 ounces per hundred pounds of seed. As a soil fungicide the chemical can be incorporated in the soil or applied to the surface usually at a rate of about 0.1 to about 50 pounds per acre. As a foliar fungicide, the toxicant is usually applied to growing plants at a rate of about 0.25 to about 10 lbs. per acre.

The compounds of this invention can be utilized as the sole pesticidal agents or they can be employed in conjunction with other bactericides, fungicides, herbicides, insecticides, acaricides, and comparable pesticides.

The following examples are presented to illustrate but a few embodiments of the invention and are not to be constructed as limiting in scope. All parts and percentages are by weight unless otherwise indicated.

EXPERIMENTAL SECTION

Example 1: N-ethyl N-hydrocgencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioates

A solution of N-ethyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate, 120.5 g (0.50 mol), in 750 ml of dry tetrahydrofuran (THF) is cooled to (-) 78° C. while being maintained under a nitrogen atmosphere. To this there is added a hexane solution, 229 ml, containing butyllithium (0.55 mol). The resulting reaction mixture is stirred for about 0.25 hr and to this there is then added all-at-once acetic-formic anhydride (0.55 mol). The resulting reaction mixture is then warmed to 0° C. over period of 2 hrs and filtered through a celite filter pad. The solvent and excess acetic-formic anhydride and acetic acid by-product are removed from the filtrate by distillation under reduced pressure to afford 118.6 g (88% of theory) of product as a clear yellow oil.

Examples 2-6 are prepared by a procedure analogous to that of Example 1 except that acetic anhydride or trifluoroacetic anhydride are substituted for acetic-formic anhydride in several of these Examples:

Example 2: N-ethyl N-methylcarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

Example 3: N-ethyl N-trifluoromethylcarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

Example 4: N-ethyl N-hydrogencarbonyl O-ethyl s-methyl phosphoroamidodithioate

Example 5: N-ethyl N-hydrogencarbonyl O-ethyl S-(5-methyl-1,2,4-oxadiazolymethyl)phosphoroamidodithioate

Example 6: N-(2,2,2-trifluoroethyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate.

Example 7: N-methyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithoate

Formic acid, 4.48 g (0.105 mol) and acetic anhydride, 7.96 g (0.078 mol) are mixed in a flask at room temperature and allowed to stand for 0.5 hr. After cooling this mixture in an ice bath, there is added N-methyl O-ethyl S-(1-methylpropyl phosphoroamidodithioate, 12 g (0.0527 mol). The resulting reaction mixture is warmed to room temperature and stirred for 1 day at room temperature. Removal of excess acetic-formic anhydride and acetic acid by-product from the resulting reaction mixture by distillation under reduced pressure affords 13.4 g (100% of theory) of product as a colorless oil.

Examples 8-15 and 49-65 are prepared by a procedure analogous to that of Example 7:

Example 8: N-methyl N-hydrogencarbonyl O-ethyl S-ethyl phosphoroamidodithioate

Example 9: N-methyl N-hydrogencarbonyl O-methyl S-(1-methylpropyl)phosphoroamidothioate

Example 10: N-methyl N-hydrogencarbonyl O-m-trifluoromethylphenyl S-(1-methylpropyl)phosphoroamidodithioate

Example 11: N-methyl N-hydrogencarbonyl O-ethyl S-propyl phosphoroamidodithioate

Example 12: N-methyl N-hydrogencarbonyl O-ethyl S-isopropyl phosphoroamidodithioate

Example 13: N-methyl N-hydrogencarbonyl O-ethyl S-tert-butyl phosphoroamidodithioate

Example 14: N-methyl N-hydrogencarbonyl O-ethyl S-(3-pentyl)phosphoroamidodithioate

Example 15: N-methyl N-hydrogencarbonyl O-ethyl S-allyl phosophoroamidodithioate

Example 16: N-ethyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

A solution of N-ethyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate, 65 g (0.24 mol), and 2,4-bis-(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetan, 60.7 g (0.15 mol) in 750 ml of 1,2-dimethoxyethane is stirred and heated at reflux temperature for about 2 hr. The resulting clear yellow solution is cooled and the solvent is removed by distillation under reduced pressure. Hexane, 1L, is added to the residue and the resulting mixture is first stirred vigorously for 0.25 hr and then allowed to stand for 0.25 hr. The hexane layer is decanted-off and the hexane is removed from this portion by distillation under reduced pressure to afford 42 g (61% of theory) of product as a yellow oil. The product can be further purified by eluting a hexane solution of the product on a chromatographic column using Bio-Sil A® (a silica gel chromatography support product available from Biorad Laboratories).

Examples 17-26 and 66-94 are prepared by a procedure analogous to that of Example 16:

Example 17: N-methylthiomethyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

Example 18: N-ethyl N-hydrogenthiocarbonyl O-ethyl S-methyl phosphoroamidodithioate

Example 19: N-methyl N-hydrogenthiocarbonyl O-ethyl S-n-propyl phosphoroamidodithoate

Example 20: N-methyl N-hydrogenthiocarbonyl O-ethyl S-isopropyl phosphoroamidodithioate

Example 21: N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

Example 22: N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

Example 23: N-allyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoramidodithioate

Example 24: N-methyl N-hydrogenthiocarbonyl O-ethyl S-tert-butyl phosphoroamidodithioate

Example 25: N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-pentyl)phosphoroamidodithioate

Example 26: N-methyl N-hydrogenthiocarbonyl O-ethyl s-(1-methylpropyl)phosphoroamidothioate

In Examples 27-37 and 95-120, a phosphoroamidothioate precursor is substituted for a phosphoroamidodithioate precursor used in Example 16.

Example 27: N-propyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

Example 28: N-butyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

Example 29: N-benzyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

Example 30: N-methylthiomethyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

Example 31: N-methyl N-hydrogenthiocarbonyl O-ethyl S-ethyl phosphoroamidothioate

Example 32: N-methyl N-hydrogenthiocarbonyl O-ethyl S-n-propyl phosphoroamidothioate

Example 33: N-methyl N-hydrogenthiocarbonyl O-ethyl S-isopropyl phosphoroamidothioate

Example 34: N-allyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

Example 35: N-methyl N-hydrogenthiocarobnyl O-ethyl S-(3-pentyl)phosphoroamidothioate

Example 36: N-ethyl N-hydrogenthiocarbonyl O-ethyl S-(3-pentyl)phosphoroamidothioate

Example 37: N-allyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

To a solution of N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate, 11.2 g (0.46 mol), and ally bromide, 9.4 g (0.056 mol), in 100 ml of methyl ethyl ketone is added powdered K₂ CO₃, 8.32 g (0.060 mol). The resulting suspension is stirred in ambient temperature for 24 hr. and then filtered. The solvent is removed from the filtrate by distillation under reduced pressure to afford 9.1 g (87% of theory) of product as a pale yellow oil. Further purification can be effected by high pressure liquid chromatography (HPLC) techniques.

Examples 38-41 and 121-146 are prepared by a procedure analogous to that of Example 37:

Example 38: N-propargyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

Example 39: N-methylthiomethyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

Example 40: N-butyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate

Example 43: Preparation of ##STR9## N-Hydrogencarbonyl N-methyl S-(1-methylpropyl)S'-propyl phosphoroamidodithioate

STEP 1 ##STR10## Preparation of N-methyl S-(1-methylpropyl)S'-propyl phosphoroamidothioate

A solution of n-propyl mercaptan (23.63 g., 0,311 moles) and triethylamine (31.41 g., 0.311 moles) in 100 ml of tetrahydrofuran is added dropwise to an ice-cooled solution of S-(1-methylpropyl)phosphorodichloridothioate (64.4 g., 0.311 moles) in 200 ml of THF. The reaction was stirred 1 hr. at R.T., then methylamine (19.3 g., 0.622 moles) is bubbled into the reaction mixture. The reaction is diluted with ether, filtered through celite to remove the triethylamine hydrochloride and methylamine hydrochloride, and evaporated to give 75 grams of product as an oil which is purified by preparative high pressure liquid chromatography (HPLC), using two prepPak 500 silica gel columns in series.

STEP 2 ##STR11##

Formic acid, 97%, (1.04 g., 0.026 moles) is added to acetic anhydride (2.10 g., 0.0206 moles) and stirred 15 min. at room temperature. The resulting formic-acetic anhydride is added to N-methyl S-(1-methylpropyl)S'-(propyl)phosphoramidodithioate (2.5 g., 0.0103 mole) and three drops of 85% phosphoric acid. The reaction is stirred 24 hours at room temperature and evaporated under high vacuum to remove acetic acid and formic-acetic anhydride, leaving 2.1 g. of material. Purification by preparative HPLC gave 0.5 of product as an oil.

Example 147: N-methylthiomethyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate

To a solution of N-hydrogencarbonyl O-ethyl S-(1-methyl-propyl)phosphoroamidothioate, 4.0 g (0.018 mol) and chloromethyl methyl sulfide, 1.84 g (0.019 mol) in 100 ml of methyl ethyl ketone is added powdered K₂ CO₃, 3.73 g (0.027 mol). The resulting suspension is stirred in ambient temperature for 24 hr. and then filtered. The solvent is removed from the filtrate by distillation under reduced pressure to afford 4.3 g (84% of theory) of product as a pale yellow oil. Further purification can be effected by high pressure liquid chromatography (HPLC) techniques.

Examples 148-179 are prepared by a procedure analogous to that of Example 147.

Table I below depicts the various substituent groups in the illustrative compounds made according to formula (I) above:

                                      TABLE I                                      __________________________________________________________________________     Tabular List of Substituents in Examples                                        ##STR12##                                                                     Example                                                                             X Y Z R.sup.1 R.sup.2     R.sup.3                                                                           R.sup.4                                      __________________________________________________________________________     1    S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                              2    S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   CH.sub.3                                                                          C.sub.2 H.sub.5                              3    S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   CF.sub.3                                                                          C.sub.2 H.sub.5                              4    S O O C.sub.2 H.sub.5                                                                        CH.sub.3    H  C.sub.2 H.sub.5                              5    S O O C.sub.2 H.sub.5                                                                         ##STR13##  H  C.sub.2 H.sub.5                              6    S O O C.sub. 2 H.sub.5                                                                        .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CF.sub.3                            7    S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     8    S O O C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                            H  CH.sub.3                                     9    S O O CH.sub.3                                                                                .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     10   S O O  .sub.--m-CF.sub.3C.sub.6 H.sub.4                                                       .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     11   S O O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.3                                     12   S O O C.sub.2 H.sub.5                                                                         .sub.-i-C.sub.3 H.sub.7                                                                   H  CH.sub.3                                     13   S O O C.sub.2 H.sub.5                                                                         .sub.-t-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     14   S O O C.sub.2 H.sub.5                                                                        CH(C.sub.2 H.sub.5).sub.2                                                                  H  CH.sub.3                                     15   S O O C.sub.2 H.sub.5                                                                        CH.sub.2 CHCH.sub.2                                                                        H  CH.sub.3                                     16   S S O C.sub.2 H.sub.5                                                                         .sub.- s-C.sub.4 H.sub.9                                                                  H  C.sub.2 H.sub.5                              17   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 SCH.sub.3                           18   S S O C.sub.2 H.sub.5                                                                        CH.sub.3    H  C.sub.2 H.sub.5                              19   S S O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.3                                     20   S S O C.sub.2 H.sub.5                                                                         .sub.-i-C.sub.3 H.sub.7                                                                   H  CH.sub.3                                     21   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  H                                            22   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     23   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH.sub.2                          24   S S O C.sub.2 H.sub.5                                                                         .sub.-t-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     25   S S O C.sub.2 H.sub.5                                                                        CH(C.sub.2 H.sub.5).sub.2                                                                  H  CH.sub.3                                     26   O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub. 9                                                                  H  CH.sub.3                                     27   O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H   -n-C.sub.3 H.sub.7                          28   O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H   -n-C.sub.4 H.sub.9                          29   O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.5                     30   O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 SCH.sub.3                           31   O S O C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                            H  CH.sub.3                                     32   O S O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.3                                     33   O S O C.sub.2 H.sub.5                                                                         .sub.-i-C.sub.3 H.sub.7                                                                   H  CH.sub.3                                     34   O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH.sub.2                          35   O S O C.sub.2 H.sub.5                                                                        CH(C.sub.2 H.sub.5).sub.2                                                                  H  CH.sub.3                                     36   O S O C.sub.2 H.sub.5                                                                        CH(C.sub.2 H.sub.5).sub.2                                                                  H  C.sub.2 H.sub.5                              37   S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH.sub.2                          38   S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCH                                39   S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 SCH.sub.3                           40   S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H   -n-C.sub.4 H.sub.9                          41   S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  H                                            42   S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CN                                  43   O O S  -n-C.sub.3 H.sub.7                                                                     .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     44   O O S  .sub.-s-C.sub.4 H.sub.9                                                                .sub.-s-C.sub. 4 H.sub.9                                                                  H  CH.sub.3                                     45   S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  H                                            46   S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CN                                  47   O S O  -n-C.sub.3 H.sub.7                                                                     .sub.-s-C.sub.4 H.sub.3                                                                   H  CH.sub.3                                     48   O S O  .sub.-s-C.sub.4 H.sub.9                                                                .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     49   S O O C.sub.2 H.sub.5                                                                         .sub.-i-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     50   S O O C.sub.2 H.sub.5                                                                         -n-C.sub.4 H.sub.9                                                                        H  CH.sub.3                                     51   S O O C.sub.2 H.sub.5                                                                         .sub.-i-C.sub.5 H.sub.11                                                                  H  CH.sub.3                                     52   S O O C.sub.2 H.sub.5                                                                        CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     H  CH.sub.3                                     53   S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.5 H.sub.11                                                                  H  CH.sub.3                                     54   S O O C.sub.2 H.sub. 5                                                                       CH.sub.2 CH.sub.2 CHCH.sub.2                                                               H  CH.sub.3                                     55   S O O C.sub.2 H.sub.5                                                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                H  CH.sub.3                                     56   S O O CH.sub.2 CF.sub.3                                                                       .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     57   S O O C.sub.2 H.sub.5                                                                        CH(C.sub.2 H.sub.5).sub.2                                                                  H  CH.sub.3                                     58   S O O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  C.sub.2 H.sub.5                              59   S O O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  H                                            60   S O O  -n-C.sub.3 H.sub.7                                                                     .sub.-s-C.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                              61   S O O  -n-C.sub.3 H.sub.7                                                                     .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     62   S O O CH.sub.2 CF.sub.3                                                                       .sub.-s-C.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                              63   S O O CH.sub.2 CH.sub.2 F                                                                     .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     64   S O O CH.sub.2 CH.sub.2 OCH.sub.3                                                             .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     65   S O O CH.sub.2 CF.sub.2 CF.sub.2 H                                                            .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     66   S S O 3-CF.sub.3 C.sub.6 H.sub.4                                                              .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     67   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 SCH.sub.3                           68   S S O C.sub.2 H.sub.5                                                                         .sub.-i-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     69   S S O C.sub.2 H.sub.5                                                                         -n-C.sub.4 H.sub.9                                                                        H  CH.sub.3                                     70   S S O C.sub.2 H.sub.5                                                                         .sub.-i-C.sub.5 H.sub.11                                                                  H  CH.sub.3                                     71   S S O C.sub.2 H.sub.5                                                                         -n-C.sub.5 H.sub.11                                                                       H  CH.sub.3                                     72   S S O C.sub.2 H.sub.5                                                                        CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     H  CH.sub.3                                     73   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.5 H.sub.11                                                                  H  CH.sub.3                                     74   S S O C.sub.2 H.sub.5                                                                        CH.sub.2 CH.sub.2 CHCH.sub.2                                                               H  CH.sub.3                                     75   S S O C.sub.2 H.sub.5                                                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                H  CH.sub.3                                     76   S S O CH.sub.2 CF.sub.3                                                                       .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     77   S S O  -n-C.sub.3 H.sub.7                                                                     .sub.-s-C.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                              78   S S O  -n-C.sub.3 H.sub.7                                                                     .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     79   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CO.sub.2 CH.sub.3                   80   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.5                     81   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 F4                  82   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 OCH.sub.33          83   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 CF.sub.33           84   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CH.sub.2 CH.sub.2 Cl                85   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 SC.sub.6 H.sub.4 Cl4                86   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C(Br)CH.sub.2                       87   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCHC.sub.6 H.sub.5                 88   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CO.sub.2 C.sub.2 H.sub.5            89   S S O C.sub.2 H.sub.5                                                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                H  CH.sub.3                                     90   S S O CH.sub.2 CF.sub.2 CF.sub.2 H                                                            .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub. 3                                    91   S S O CH.sub.2 CF.sub.3                                                                       .sub.-s-C.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                              92   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 SC.sub.6 H.sub.5                    93   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCHCH.sub.3                        94   S S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 NO.sub.24           95   O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CCH                                 96   O S O CH.sub.2 CF.sub.3                                                                       .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     97   O S O C.sub.2 H.sub.5                                                                        CH.sub.2 CHCH.sub.2                                                                        H  CH.sub.3                                     98   O S O C.sub.2 H.sub.5                                                                        s-C.sub.4 H.sub.9                                                                          H  CH.sub.3                                     99   O S O C.sub.2 H.sub.5                                                                         -n-C.sub.4 H.sub.9                                                                        H  CH.sub.3                                     100  O S O C.sub.2 H.sub.5                                                                        CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     H  CH.sub.3                                     101  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.5 H.sub.11                                                                  H  CH.sub.3                                     102  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  C.sub.2 H.sub.5                              103  O S O  -n-C.sub.3 H.sub.7                                                                     .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     104  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 F4                  105  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 OCH.sub.33          106  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 CF.sub.33           107  O S O CH.sub.2 CH.sub.2 F                                                                     .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.3                                     108  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub. 9                                                                  H  CH.sub.2 CHCHCH.sub.3                        109  O S O C.sub.2 H.sub.5                                                                        C.sub.3 H.sub.7                                                                            H  CH.sub.2 CHCH.sub.2                          110  O S O C.sub.2 H.sub.5                                                                        C.sub.3 H.sub.7                                                                            H  CH.sub.2 CCH                                 111  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.10 H.sub.7                    112  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 Br2                 113  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.3 ClF2,6              113  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.3 ClF2,6              114  O S O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H   -n-C.sub.3 H.sub.7                          115  O S O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H   -n-C.sub. 4 H.sub.9                         116  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.3 CH.sub.3                                              NO.sub.23,4                                  117  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 F.sub.52,3,4,5,6            118  O S O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.3 Cl.sub.22,6         119  O S O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.2 C.sub.6 H.sub.5                     120  O S O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.2 CO.sub.2 CH.sub.3                   121  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CO.sub.2 CH.sub.3                   122  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.5                     123  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 F4                  124  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 OCH.sub.33          125  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 CF.sub.33           126  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CH.sub.2 CH.sub.2 Cl                127  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 SC.sub.6 H.sub.4 Cl4                128  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C(Br)CH.sub.2                       129  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCHC.sub.6 H.sub.5                 130  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CO.sub.2 C.sub.2 H.sub.5            131  S O O C.sub.2 H.sub.5                                                                         -n-C.sub.4 H.sub.9                                                                        H  CH.sub.2 C.sub.6 H.sub.4 NO.sub.24           132  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 CN4                 133  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C(O)C.sub.6 H.sub.5                 134  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 Br2                 135  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 OC.sub.6 H.sub.4 Cl4                136  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.10 H.sub.7                    137  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCHCH.sub.3                        138  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.3 ClF2,6              139  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub. 9                                                                  H  CH.sub.2 C.sub.6 F.sub.52,3,4,5,6            140  S O O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H   -n-C.sub.4 H.sub.9                          141  S O O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.2 C.sub.6 H.sub.5                     142  S O O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.2 CO.sub.2 C.sub.2 H.sub.5            143  S O O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.2 CH.sub.2 CH.sub.2 Cl                144  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 OCH.sub.2                                             C.sub.6 H.sub.5                              145  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H                                                                                  ##STR14##                                   146  S O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C(CH.sub.3)CH.sub.2                 147  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 SCH.sub.3                           148  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.5                     149  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CN                                  150  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 OCH.sub.3                           151  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CH.sub.2 CH.sub.2 Cl                152  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 F4                  153  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 OCH.sub.33          154  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 CF.sub.33           155  O O O C.sub.2 H.sub. 5                                                                        .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 SC.sub.6 H.sub.4 Cl4                156  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CHCHC.sub.6 H.sub.5                 157  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 SC.sub.6 H.sub.5                    158  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 CH.sub.32           159  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 NO.sub.24           160  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 CH.sub.2 CH.sub.2 Cl                161  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C(O)C.sub.6 H.sub.5                 162  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.10 H.sub.7                    163  O O O C.sub. 2 H.sub.5                                                                        .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 Br2                 164  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.2 H.sub.3 ClF2,6              165  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 F.sub.52,3,4,5,6            166  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.3 Cl.sub.22,6         167  O O O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.2 C.sub.6 H.sub.5                     168  O O O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.2 C.sub.6 H.sub.4 F4                  169  O O O C.sub.2 H.sub.5                                                                        n-C.sub.3 H.sub.7                                                                          H  CH.sub.2 C.sub.6 H.sub.3 ClF2,6              170  O O O CH.sub.2 CH.sub.2 F                                                                     .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.5                     171  O O O CH.sub.2 CH.sub.2 F                                                                     .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 NO.sub.24           172  O O O C.sub.2 H.sub.5                                                                         -n-C.sub.3 H.sub.7                                                                        H  CH.sub.2 C.sub.6 H.sub.4 CF.sub.33           173  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H(CH.sub.3).sub.42,3,5,                                       6                                            174  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 C(O)CH.sub.33       175  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 CH.sub.32           176  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.3 CH.sub.3                                              NO.sub.23,4                                  177  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 F3                  178  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub. 9                                                                  H  CH.sub.2 C.sub.6 H.sub.3 Cl.sub.23,4         179  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.3 (CH.sub.3).sub.                                       22,5                                         180  O O O C.sub.2 H.sub.5                                                                         .sub.-s-C.sub.4 H.sub.9                                                                   H  CH.sub.2 C.sub.6 H.sub.4 CN4                 __________________________________________________________________________

Tables II and III which follow, respectively, set forth the analytical data and nuclear magnetic resonance (nmr) data of representative compounds selected from Table I.

                  TABLE II                                                         ______________________________________                                         Elemental Analysis                                                             Ex-                 % Calcd. (Found)                                           ample Emp. Formula  C         H      N                                         ______________________________________                                          1    C.sub.9 H.sub.20 NO.sub.2 PS.sub.2                                                           40.10(39.21)                                                                             7.50(7.54)                                                                            5.20(4.66)                                 2    NA                                                                        3    C.sub.10 H.sub.19 F.sub.3 NO.sub.2 PS.sub.2                                                  35.59(36.30)                                                                             5.68(5.40)                                                                            4.15(4.13)                                 4    C.sub.6 H.sub.14 NOPS.sub.2                                                                  34.10(33.99)                                                                             6.68(6.23)                                                                            6.63(6.29)                                 5    NA                                                                        6    NA                                                                        7    C.sub.8 H.sub.18 NO.sub.2 PS.sub.2                                                           37.60(38.10)                                                                             7.10(7.05)                                                                            5.48(5.49)                                 8    C.sub.6 H.sub.14 NO.sub.2 PS.sub.2                                                           31.71(31.41)                                                                             6.21(6.43)                                                                            6.16(6.16)                                 9    C.sub.7 H.sub.16 NO.sub.2 PS.sub.2                                                           34.83(35.13)                                                                             6.68(6.97)                                                                            5.80(5.56)                                 10   NA                                                                        11   C.sub.7 H.sub.16 NO.sub.2 PS.sub.2                                                           34.83(34.39)                                                                             6.68(6.34)                                                                            5.80(6.12)                                 12   C.sub.7 H.sub.16 NO.sub.2 PS.sub.2                                                           34.84(34.97)                                                                             6.68(6.80)                                                                            5.80(5.65)                                 13   C.sub.8 H.sub.18 NO.sub.2 PS.sub.2                                                           37.62(36.81)                                                                             7.10(7.02)                                                                            5.48(6.19)                                 14   C.sub.9 H.sub.20 NO.sub.2 PS.sub.2                                                           40.13(41.04)                                                                             7.48(7.64)                                                                            5.20(5.09)                                 15   NA                                                                        16   C.sub.9 H.sub.20 NOPS.sub.3                                                                  37.87(39.58)                                                                             7.06(7.38)                                                                            4.91(4.99)                                 17   NA                                                                        18   C.sub.9 H.sub.20 NOPS.sub.4                                                                  34.00(35.74)                                                                             6.34(6.65)                                                                            4.41(3.78)                                 19   NA                                                                        20   NA                                                                        21   C.sub.6 H.sub.14 NOPS.sub.3                                                                  29.61(30.48)                                                                             5.80(5.76)                                                                            5.76(5.88)                                 22   C.sub.7 H.sub.16 NOPS.sub.3                                                                  32.66(33.61)                                                                             6.27(7.06)                                                                            5.44(6.57)                                 23   C.sub.7 H.sub.16 NOPS.sub.3                                                                  32.66(32.48)                                                                             6.27(6.09)                                                                            5.44(5.28)                                 24   C.sub.7 H.sub.16 NOPS.sub.3                                                                  32.66(33.14)                                                                             6.26(6.42)                                                                            5.44(5.65)                                 25   C.sub.8 H.sub.18 NOPS.sub.3                                                                  35.40(36.16)                                                                             6.68(6.93)                                                                            5.16(5.36)                                 26   C.sub.10 H.sub.20 NOPS.sub.3                                                                 40.37(40.46)                                                                             6.77(7.24)                                                                            4.70(5.12)                                 27   C.sub.8 H.sub.18 NOPS.sub.3                                                                  35.40(35.75)                                                                             6.68(6.85)                                                                            5.16(5.35)                                 28   C.sub.9 H.sub.20 NOPS.sub.3                                                                  37.87(38.73)                                                                             7.06(7.17)                                                                            4.91(5.26)                                 29   C.sub.8 H.sub.18 NO.sub.2 PS.sub.2                                                           37.62(36.06)                                                                             7.10(7.09)                                                                            5.48(5.58)                                 30   C.sub.10 H.sub.22 NO.sub.2 PS.sub.2                                                          42.30(42.20)                                                                             7.82(7.91)                                                                            4.94(4.88)                                 31   C.sub.11 H.sub.24 NO.sub.2 PS.sub.2                                                          44.40(44.20)                                                                             8.13(8.16)                                                                            4.70(4.72)                                 32   C.sub.14 H.sub.22 NO.sub.2 PS.sub.2                                                          50.73(49.74)                                                                             6.69(6.73)                                                                            4.22(4.29)                                 33   C.sub.9 H.sub.20 NO.sub.2 PS.sub.3                                                           35.85(35.85)                                                                             6.68(6.53)                                                                            4.64(4.77)                                 34   C.sub.6 H.sub.14 NO.sub.2 PS.sub.2                                                           31.70(31.14)                                                                             6.21(6.95)                                                                            6.16(6.35)                                 35   C.sub.7 H.sub.16 NO.sub.2 PS.sub.2                                                           34.83(34.24)                                                                             6.68(6.71)                                                                            5.80(5.78)                                 36   C.sub.7 H.sub.16 NO.sub.2 PS.sub.2                                                           34.84(34.38)                                                                             6.68(6.88)                                                                            5.80(5.91)                                 37   C.sub.10 H.sub.20 NO.sub.2 PS.sub.2                                                          42.68(41.74)                                                                             7.16(7.22)                                                                            4.97(5.12)                                 38   C.sub.9 H.sub.20 NO.sub.2 PS.sub.2                                                           40.13(39.96)                                                                             7.48(7.65)                                                                            5.20(5.35)                                 39   C.sub.10 H.sub.22 NO.sub.2 PS.sub.2                                                          42.65(42.28)                                                                             8.29(7.94)                                                                            5.24(5.29)                                 40   C.sub.10 H.sub.20 NO.sub.2 PS.sub.2                                                          42.68(42.71)                                                                             7.16(7.31)                                                                            4.97(5.15)                                 41   C.sub.10 H.sub.18 NO.sub.2 PS.sub.3                                                          42.99(42.41)                                                                             6.49(6.23)                                                                            5.01(5.34)                                 42   C.sub.9 H.sub.20 NO.sub.2 PS.sub.3                                                           35.85(35.98)                                                                             6.68(6.55)                                                                            4.64(4.76)                                 43   NA                                                                        44   C.sub.11 H.sub.24 NO.sub.2 PS.sub.2                                                          44.41(44.07)                                                                             8.13(8.12)                                                                            4.70(4.79)                                 45   C.sub.7 H.sub.16 NO.sub.2 PS.sub.2                                                           34.8(35.16)                                                                              6.70(6.83)                                                                            5.80(4.87)                                 46   C.sub.9 H.sub.17 N.sub.2 O.sub.2 PS.sub.2                                                    38.55(38.07)                                                                             6.11(6.16)                                                                            9.99(9.61)                                 47                                                                             48                                                                             49   C.sub.8 H.sub.18 NO.sub.2 PS.sub.2                                                           37.62(37.64)                                                                             7.10(6.99)                                                                            5.48(5.36)                                 50   C.sub.8 H.sub.18 NO.sub.2 PS.sub.2                                                           37.62(37.53)                                                                             7.10(6.99)                                                                            5.48(5.56)                                 51   C.sub.9 H.sub.20 NO.sub.2 PS.sub.2                                                           40.12(39.88)                                                                             7.48(7.54)                                                                            5.20(5.28)                                 52   C.sub.9 H.sub.20 NO.sub.2 PS.sub.2                                                           40.12(40.32)                                                                             7.48(7.58)                                                                            5.20(5.42)                                 53   C.sub.8 H.sub.16 NO.sub.2 PS.sub.2                                                           37.92(38.42)                                                                             6.36(6.55)                                                                            5.52(5.67)                                 54   C.sub.8 H.sub.16 NO.sub.2 PS.sub.2                                                           37.92(38.42)                                                                             6.36(6.55)                                                                            5.52(5.67)                                 55   C.sub.7 H.sub.16 NO.sub.3 PS.sub.2                                                           32.67(31.96)                                                                             6.26(6.19)                                                                            5.44(4.99)                                 56   NA                                                                        57   NA                                                                        58   NA                                                                        59   NA                                                                        60   NA                                                                        61   NA                                                                        62   NA                                                                        63   C.sub.8 H.sub.17 FNO.sub.2 PS.sub.2                                                          35.15(35.67)                                                                             6.27(5.98)                                                                            5.12(4.69)                                 64   C.sub.9 H.sub.20 NO.sub.3 PS.sub.2                                                           37.88(37.73)                                                                             7.06(7.16)                                                                            4.91(4.73)                                 65   C.sub.9 H.sub.16 F.sub.4 NO.sub.2 PS.sub.2                                                   31.67(32.18)                                                                             4.73(4.70)                                                                            4.10(3.29)                                 66   C.sub.13 H.sub.17 F.sub.3 NOPS.sub.3                                                         40.29(41.98)                                                                             4.42(5.24)                                                                            3.62(3.72)                                 67   C.sub.9 H.sub.20 NOPS.sub.4                                                                  34.40(35.74)                                                                             6.34(6.65)                                                                            4.41(3.55)                                 68   C.sub.8 H.sub.18 NOPS.sub.3                                                                  35.40(35.49)                                                                             6.68(6.54)                                                                            5.16(5.02)                                 69   C.sub.8 H.sub.18 NOPS.sub.3                                                                  35.40(35.96)                                                                             6.68(6.70)                                                                            5.16(5.21)                                 70   C.sub.9 H.sub.20 NOPS.sub.3                                                                  37.86(39.03)                                                                             7.06(7.48)                                                                            4.90(4.94)                                 71   C.sub.9 H.sub.22 NOPS.sub.3                                                                  37.86(38.84)                                                                             7.06(7.42)                                                                            4.90(5.13)                                 72   C.sub.9 H.sub.20 NOPS.sub.3                                                                  37.86(39.48)                                                                             7.06(7.42)                                                                            4.90(4.80)                                 73   C.sub.9 H.sub.20 NOPS.sub.3                                                                  37.86(39.26)                                                                             7.06(7.62)                                                                            4.9(4.95)                                  74   C.sub.8 H.sub.16 NOPS.sub.3                                                                  35.66(37.50)                                                                             5.98(6.57)                                                                            5.19(6.57)                                 75   C.sub.7 H.sub.16 NO.sub.1 PS.sub.3                                                           30.75(31.79)                                                                             5.90(6.20)                                                                            5.12(4.65)                                 76   NA                                                                        77   NA                                                                        78   NA                                                                        79   C.sub.10 H.sub.20 NO.sub.3 PS.sub.3                                                          36.45(37.01)                                                                             6.11(6.31)                                                                            4.25(4.57)                                 80   C.sub.14 H.sub.22 NOPS.sub.3                                                                 48.38(50.57)                                                                             6.38(6.44)                                                                            4.03(3.82)                                 81   C.sub.14 H.sub.21 FNOPS.sub.3                                                                46.0(45.73)                                                                              5.79(5.67)                                                                            3.83(3.70)                                 82   C.sub.15 H.sub.24 NO.sub.2 PS.sub.3                                                          47.71(47.97)                                                                             6.40(6.65)                                                                            3.71(3.69)                                 83   C.sub.15 H.sub.21 F.sub.3 NOPS.sub.3                                                         43.35(44.76)                                                                             5.09(5.12)                                                                            3.37(3.13)                                 84   C.sub.10 H.sub.21 CLNOPS.sub.3                                                               35.96(36.60)                                                                             6.34(6.60)                                                                            4.19(3.74)                                 85   C.sub.14 H.sub.21 CLNOPS.sub.4                                                               40.6(43.04)                                                                              5.10(5.20)                                                                            3.38(2.82)                                 86   C.sub.10 H.sub.19 BrNOPS.sub.3                                                               31.91(32.67)                                                                             5.08(5.34)                                                                            3.72(3.33)                                 87   C.sub.16 H.sub.24 NOPS.sub.3                                                                 51.4(51.18)                                                                              6.47(6.60)                                                                            3.75(3.99)                                 88   C.sub.11 H.sub.22 NO.sub.3 PS.sub.3                                                          38.46(38.85)                                                                             6.45(6.68)                                                                            4.07(4.22)                                 89   C.sub.11 H.sub.24 NO.sub.2 PS.sub.3                                                          40.09(38.79)                                                                             7.34(6.71)                                                                            4.25(4.11)                                 90   NA                                                                        91   NA                                                                        92   NA                                                                        93   NA                                                                        94                                                                             95   C.sub.10 H.sub.18 NO.sub.2 PS.sub.2                                                          42.99(40.58)                                                                             6.49(6.86)                                                                            5.01(4.81)                                 96   C.sub.8 H.sub.15 F.sub.3 NO.sub.2 PS.sub.2                                                   31.06(31.69)                                                                             4.89(4.80)                                                                            4.52(4.60)                                 97   C.sub.7 H.sub.14 NO.sub.2 PS.sub.2                                                           35.13(35.10)                                                                             5.89(6.03)                                                                            5.85(5.97)                                 98   C.sub.8 H.sub.18 NO.sub.2 PS.sub.2                                                           37.62(37.80)                                                                             7.10(7.12)                                                                            5.48(5.72)                                 99   C.sub.9 H.sub.20 NO.sub.2 PS.sub.2                                                           40.10(39.58)                                                                             7.48(7.55)                                                                            5.20(5.01)                                100   C.sub.9 H.sub.20 NO.sub.2 PS.sub.2                                                           40.10(39.60)                                                                             7.48(7.67)                                                                            5.20(5.18)                                101   C.sub.9 H.sub.20 NO.sub.2 PS.sub.2                                                           40.10(38.83)                                                                             7.48(7.48)                                                                            5.20(4.87)                                102   NA                                                                       103   NA                                                                       104   C.sub.14 H.sub.21 FNO.sub.2 PS.sub.2                                                         48.11(48.01)                                                                             6.05(6.10)                                                                            4.00(4.04)                                105   C.sub.15 H.sub.24 NO.sub.3 PS.sub.2                                                          49.84(49.59)                                                                             6.69(6.44)                                                                            3.87(4.23)                                106   C.sub.15 H.sub.21 F.sub.3 NO.sub.2 PS.sub.2                                                  45.10(45.18)                                                                             5.30(5.48)                                                                            3.50(3.44)                                107   NA                                                                       108   C.sub.11 H.sub.22 NO.sub.2 PS.sub.2                                                          44.72(44.52)                                                                             7.50(7.65)                                                                            4.74(4.90)                                109   C.sub.9 H.sub.18 NO.sub.2 PS.sub.2                                                           40.4(37.86)                                                                              6.78(6.91)                                                                            5.23(6.13)                                110   C.sub.9 H.sub.16 NO.sub.2 PS.sub.2                                                           40.73(40.49)                                                                             6.07(6.32)                                                                            5.27(5.35)                                111   C.sub.18 H.sub.24 NO.sub.2 PS.sub.2                                                          56.66(55.68)                                                                             6.34(6.49)                                                                            3.67(3.42)                                112   C.sub.14 H.sub.21 BrNO.sub.2 PS.sub.2                                                        40.97(41.43)                                                                             5.15(5.12)                                                                            3.41(3.42)                                113   C.sub.14 H.sub.20 ClFNO.sub.2 PS.sub.2                                                       43.80(44.35)                                                                             5.25(4.68)                                                                            3.64(2.33)                                114   C.sub.9 H.sub.20 NO.sub.2 PS.sub.2                                                           40.12(40.45)                                                                             7.48(6.74)                                                                            5.20(4.16)                                115   C.sub.10 H.sub.22 NO.sub.2 PS.sub.2                                                          42.37(41.58)                                                                             7.82(7.66)                                                                            4.94(4.82)                                116   C.sub.15 H.sub.23 N.sub.2 O.sub.5 PS.sub.2                                                   48.11(47.80)                                                                             6.19(6.52)                                                                            7.48(7.33)                                117   C.sub.14 H.sub.17 F.sub.5 NO.sub.2 PS.sub.2                                                  39.90(40.14)                                                                             4.06(4.16)                                                                            3.32(3.60)                                118   C.sub.14 H.sub.20 Cl.sub.2 NO.sub.2 PS.sub.2                                                 42.00(41.93)                                                                             5.03(4.88)                                                                            3.49(2.77)                                119   NA                                                                       120   NA                                                                       121   C.sub.10 H.sub.20 NO.sub.4 PS.sub.2                                                          38.32(38.48)                                                                             6.43(6.60)                                                                            4.47(4.88)                                122   C.sub.14 H.sub.22 NO.sub.2 PS.sub.2                                                          50.73(52.49)                                                                             6.69(6.86)                                                                            4.22(3.95)                                123   C.sub.14 H.sub.21 FNO.sub.2 PS.sub.2                                                         48.11(46.97)                                                                             6.00(6.02)                                                                            4.00(3.76)                                124   C.sub.15 H.sub.24 NO.sub.3 PS.sub.2                                                          49.84(49.17)                                                                             6.69(6.71)                                                                            3.87(3.72)                                125   C.sub.15 H.sub.21 F.sub.3 NO.sub.2 PS.sub.2                                                  45.10(45.60)                                                                             5.30(5.45)                                                                            3.50(3.72)                                126   C.sub.10 H.sub.21 ClNO.sub.2 PS.sub.2                                                        37.78(36.90)                                                                             6.66(6.74)                                                                            4.40(4.65)                                127   C.sub.14 H.sub.21 ClNO.sub.2 PS.sub.2                                                        42.25(42.01)                                                                             5.31(5.49)                                                                            3.52(3.80)                                128   C.sub.10 H.sub.19 BrNO.sub.2 PS.sub.2                                                        33.30(33.93)                                                                             5.31(5.41)                                                                            22.18(20.64)                              129   C.sub.16 H.sub.24 NO.sub.2 PS.sub.2                                                          53.75(53.71)                                                                             6.70(6.72)                                                                            3.91(3.96)                                130   C.sub.11 H.sub.22 NO.sub.4 PS.sub.2                                                          40.35(40.31)                                                                             6.77(6.87)                                                                            4.27(4.67)                                131   C.sub.14 H.sub.21 N.sub.2 O.sub.4 PS.sub.2                                                   44.60(43.52)                                                                             5.62(5.74)                                                                            7.44(7.21)                                132   C.sub.15 H.sub.21 N.sub.2 O.sub.2 PS.sub.2                                                   50.50(50.59)                                                                             5.93(6.08)                                                                            7.86(7.74)                                133   C.sub.15 H.sub.22 NO.sub.3 PS.sub.2                                                          50.10(47.67)                                                                             6.17(6.49)                                                                            3.89(4.11)                                134   C.sub.14 H.sub.21 BrNO.sub.2 PS.sub.2                                                        40.97(40.86)                                                                             5.15(5.01)                                                                            3.41(2.98)                                135   C.sub.14 H.sub.21 ClNO.sub.3 PS.sub.2                                                        44.02(43.64)                                                                             5.54(5.55)                                                                            3.66(3.60)                                136   C.sub.18 H.sub.24 NO.sub.2 PS.sub.2                                                          56.60(55.96)                                                                             6.34(6.13)                                                                            3.67(3.47)                                137   C.sub.11 H.sub.22 NO.sub.2 PS.sub.2                                                          44.72(44.25)                                                                             7.50(7.71)                                                                            4.74(4.62)                                138   C.sub.14 H.sub.20 ClFNO.sub.2 PS.sub.2                                                       43.80(43.63)                                                                             5.25(5.29)                                                                            3.64(3.47)                                139   C.sub.14 H.sub.17 F.sub.5 NO.sub.2 PS.sub.2                                                  39.90(39.99)                                                                             4.06(4.13)                                                                            3.32(3.45)                                140   C.sub.10 H.sub.22 NO.sub.2 PS.sub.2                                                          42.37(42.10)                                                                             7.82(7.58)                                                                            4.94(5.30)                                141   C.sub.13 H.sub.20 NO.sub.2 PS.sub.2                                                          49.18(49.13)                                                                             6.35(6.34)                                                                            4.41(4.79)                                142   C.sub.10 H.sub.20 NO.sub.4 PS.sub.2                                                          38.30(38.21)                                                                             6.43(6.53)                                                                            4.46(4.76)                                143   C.sub.9 H.sub.19 ClNO.sub.2 PS.sub.2                                                         35.57(35.34)                                                                             6.30(6.36)                                                                            4.61(4.81)                                144   C.sub.21 H.sub.28 NO.sub.3 PS.sub.2                                                          57.64(55.83)                                                                             6.44(6.43)                                                                            3.20(3.49)                                145   C.sub.15 H.sub.21 ClNO.sub.4 PS.sub.2                                                        43.95(43.74)                                                                             5.16(5.22)                                                                            3.41(3.48)                                146   C.sub.11 H.sub.22 NO.sub.2 PS.sub.2                                                          44.72(44.55)                                                                             7.50(7.46)                                                                            4.74(4.62)                                147   C.sub.9 H.sub.20 NO.sub.3 PS.sub.2                                                           37.8(38.09)                                                                              7.10(7.36)                                                                            4.6(5.45)                                 148   C.sub.14 H.sub.22 NO.sub.3 PS                                                                53.3(54.74)                                                                              7.00(7.23)                                                                            4.4(5.20)                                 149   C.sub.9 H.sub.17 N.sub.2 O.sub.3 PS                                                          40.89(41.03)                                                                             6.48(6.74)                                                                            10.60(10.05)                              150   C.sub.9 H.sub.20 NO.sub.4 PS                                                                 40.10(40.71)                                                                             7.48(8.00)                                                                            5.20(4.68)                                151   C.sub.10 H.sub.21 ClNO.sub.3 PS                                                              39.79(38.14)                                                                             7.00(7.00)                                                                            4.64(4.58)                                152   C.sub.14 H.sub.21 FNO.sub.3 PS                                                               50.43(50.64)                                                                             6.35(6.44)                                                                            4.20(4.21)                                153   C.sub.15 H.sub.24 NO.sub.4 PS                                                                52.15(51.79)                                                                             7.00(7.04)                                                                            4.05(4.38)                                154   C.sub.15 H.sub.21 F.sub.3 NO.sub.3 PS                                                        46.99(47.57)                                                                             5.52(5.69)                                                                            3.65(3.60)                                155   C.sub.14 H.sub.21 ClNO.sub.3 PS.sub.2                                                        44.00(43.80)                                                                             5.54(572)                                                                             3.66(3.81)                                156   C.sub.16 H.sub.24 NO.sub.3 PS                                                                56.28(55.80)                                                                             7.08(7.08)                                                                            4.10(3.92)                                157   C.sub.14 H.sub.22 NO.sub.3 PS                                                                48.39(48.54)                                                                             6.38(6.57)                                                                            4.03(4.11)                                158   C.sub.15 H.sub.24 NO.sub.3 PS                                                                54.69(54.01)                                                                             7.34(7.56)                                                                            4.25(4.29)                                159   C.sub.14 H.sub.21 N.sub.2 O.sub.5 PS                                                         46.65(46.33)                                                                             5.83(6.11)                                                                            7.77(7.56)                                160   C.sub.9 H.sub.19 ClNO.sub.3 PS                                                               37.56(36.96)                                                                             6.65(6.80)                                                                            4.86(4.75)                                161   C.sub.15 H.sub.22 NO.sub.4 PS                                                                52.46(51.71)                                                                             6.45(6.83)                                                                            4.07(4.29)                                162   C.sub.18 H.sub.24 NO.sub.3 PS                                                                59.15(59.26)                                                                             6.61(6.79)                                                                            3.83(3L85)                                163   C.sub.14 H.sub.21 BrNO.sub.3 PS                                                              42.64(42.89)                                                                             5.36(5.48)                                                                            3.55(3.44)                                164   C.sub.14 H.sub.20 ClFNO.sub.3 PS                                                             45.71(45.60)                                                                             5.48(5.66)                                                                            3.80(3.91)                                165   C.sub.14 H.sub.17 F.sub.5 NO.sub.3 PA                                                        41.48(41.54)                                                                             4.22(3.95)                                                                            3.45(3.66)                                166   C.sub.14 H.sub.10 Cl.sub.2 NO.sub.3 PS                                                       43.75(43.47)                                                                             5.24(5.31)                                                                            3.64(3.88)                                167   C.sub.13 H.sub.20 NO.sub.3 PS                                                                51.8(52.25)                                                                              6.69(6.59)                                                                            4.64(4.76)                                168   C.sub.13 H.sub.19 FNO.sub.3 PS                                                               48.89(48.56)                                                                             5.99(6.05)                                                                            4.38(4.66)                                169   C.sub.13 H.sub.18 ClFNO.sub.3 PS                                                             44.10(43.84)                                                                             5.12(5.32)                                                                            3.95(4.03)                                170   C.sub.14 H.sub.21 FNO.sub.3 PS                                                               50.44(49.90)                                                                             6.35(6.61)                                                                            4.20(4.83)                                171   C.sub.14 H.sub.20 FN.sub.2 O.sub.5 PS                                                        50.78(49.03)                                                                             5.33(5.31)                                                                            7.40(7.34)                                172   C.sub.14 H.sub.19 F.sub.3 NO.sub.3 PS                                                        45.52(45.52)                                                                             5.18(5.11)                                                                            3.79(3.84)                                173   C.sub.18 H.sub.18 NO.sub.2 PS                                                                19.64(50.10)                                                                             6.94(6.80)                                                                            3.21(3.45)                                174   C.sub.16 H.sub.24 NO.sub.4 PS                                                                53.76(52.53)                                                                             6.76(6.56)                                                                            3.91(3.82)                                175   C.sub.15 H.sub.24 NO.sub.3 PS                                                                54.69(54.68)                                                                             7.34(7.29)                                                                            4.25(4.16)                                176   C.sub.15 H.sub.23 N.sub.2 O.sub.5 PS                                                         48.11(47.80)                                                                             6.19(6.52)                                                                            7.48(7.33)                                177   NA                                                                       178   C.sub.14 H.sub.20 Cl.sub.2 NO.sub.3 PS                                                       43.75(43.74)                                                                             5.24(5.27)                                                                            3.64(3.56)                                179   NA                                                                       180   C.sub.15 H.sub.21 N.sub.2 O.sub.3 PS                                                         52.92(52.20)                                                                             6.21(6.54)                                                                            8.23(8.11)                                ______________________________________                                    

                  TABLE III                                                        ______________________________________                                         Nuclear Magnetic Resonance Data (ppm, δ)                                 ______________________________________                                         Example 1: 8.90(s, 1H, CCH); 4.30(m, 2H, OCH.sub.2 CH.sub.3); 3.68(m,          1H,                                                                            SCH) 3.60(m, 2H, NCH.sub.2); 1.64(m, 2H, SCHCH.sub.2); 1.40(m, 3H,             SCH(CH.sub.3); 1.40 (t, 3H, OCH.sub.2 CH.sub.3); 1.40(t, 3H, NCH.sub.2         CH.sub.3);                                                                     1.20(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 2: 4.20(m, 2H, OCH.sub.2); 3.80(m, 2H, NCH.sub.2), 3.40(m, 1H,         SCH), 2.20(s, 3H, NCOCH.sub.3); 1.64(m, 2H, SCHCH.sub.2); 1.40(t, 3H,          OCH.sub.2 CH.sub.3); 1.40 (t, 3H, NCH.sub.2 CH.sub.3); 1.40(m, 3H,             SCHCH.sub.3);                                                                  1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 3: 4.30(m, 2H, OCH.sub.2); 3.80(m, 2H, NCH.sub.2), 3.40(m, 1H,         SCH); 1.64(m, 2H, SCHCH.sub.2); 1.40(t, 3H, OCH.sub.2 CH.sub.3); 1.40(t,       3H,                                                                            NCH.sub.2 CH.sub.3); 1.40 (3H, SCHCH.sub.3); 1.00(m, 3H,                       SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                                Example 4: 8.88(s, 1H, OCH); 4.38(m, 2H, OCH.sub.2); 3.70(m, 2H,               NCH.sub.2); 2.41(d, 3H, SCH.sub.3); 1.40(q, 6H, NCH.sub.2 CH.sub.3 and         OCH.sub.2 CH.sub.3)                                                            Example 5: 8.90(s, 1H, OCH); 4.38(m, 2H, OCH.sub.2); 4.30(d, 2H,               SCH.sub.2); 3.58(m, 2H, NCH.sub.2); 2.58(s, 3H, ring CH.sub.3); 1.38(m,        6H,                                                                            NCH.sub.2 CH.sub.3 and OCH.sub.2 CH.sub.3)                                     Example 6: 8.75(s, 1H, OCH); 4.40(m, 4H, OCH.sub.2 and NCH.sub.2);             3.58(m, 1H, SCH); 1.84(m, 2H, SCHCH.sub.2); 1.50(m, D6H, OCH.sub.2             CH.sub.3                                                                       and SCHCH.sub.3); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                  Example 7: 8.90(s, 1H, OCH); 4.30(m, 2H, OCH.sub.2); 3.48(m, 1H,               SCH); 308(d, 3H, NCH.sub.3)D; 1.78(m, 2H, SCHCH.sub.2); 1.38(t, 6H,            OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.08(m, 3H, SCH(CH.sub.3)CH.sub.2         CH.sub.3)                                                                      Example 8: 8.92(s, 1H, OCH); 4.38(m, 2H, OCH.sub.2); 3.15(m, 2H,               SCH.sub.2) 3.08(d, 3H, NCH.sub.3); 1.38(dt, 6H, SCH.sub.2 CH.sub.3 and         OCH.sub.2 CH.sub.3)                                                            Example 9: 8.90(s, 1H, OCH); 3.80(d, 3H, OCH.sub.3); 3.40(m, 1H, SCH),         3.00(d, 3H, NCH.sub.3); 1.70(m, 2H, SCHCH.sub.2); 1.40(t, 6H, OCH.sub.2        CH.sub.3                                                                       and SCHCH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                  Example 10: 8.85(s, 1H, OCH); 7.50(s, 4H, aromatic); 3.50(m, 1H,               SCH); 3.19(d, 3H, NCH.sub.3); 1.70(m, 2H, SCHCH.sub.2); 1.38(d, 3H,            SCHCH.sub.3); 0.98 (m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                     Example 11: 8.90(s, 1H, OCH); 4.30(m, 2H, OCH.sub.2); 3.00(d, 3H,              NCH.sub.3); 2.80(m, 2H, SCH.sub.2); 1.78(m, 2H, SCH.sub.2 CH.sub.2);           1.40(t, 3H,                                                                    OCH.sub.2 CH.sub.3); 1.00 (t, 3H, SCH.sub.2 CH.sub.2 CH.sub.3)                 Example 12: 8.88(s, 1H, OCH); 4.25(m, 2H, OCH.sub.2); 3.50(m, 1H,              SC.sub.--H), 3.02(d, 3H, NCH.sub.3); 1.20(m, 9H, OCH.sub.2 CH.sub.3 and        SCH(CH.sub.3).sub.2                                                            Example 13: 8.90(s, 1H, OCH); 4.20(m, 2H, OCH.sub.2); 2.98(d, 3H,              NCH.sub.3); 1.58(d, 9H, SCH(CH.sub.3).sub.3 ; 1.30(t, 3H, OCH.sub.2            CH.sub.3)                                                                      Example 14: 8.90(s, 1H, OCH); 4.30(m, 2H, OCH.sub.2); 3.42(m, 1H,              SCH); 1.78(m, 4H, SCH(CH.sub.2 CH.sub.3).sub.2 ; 1.50(t, 3H, OCH.sub.2         CH.sub.3);                                                                     1.10(m, 6H, SCH (CH.sub.2 CH.sub.3).sub.2                                      Example 15: 8.95(s, 1H, OCH); 5.90(m, 1H, SCH.sub.2 CH═CH.sub.2);          5.36(m, 2H, SCH.sub.2 CH═CH.sub.2); 4.30(m, 2H, OCH.sub.2); 3.60(m,        2H,                                                                            SCH.sub.2 CH═CH.sub.2); 3.00(d, 3H NCH.sub.3); 1.40(t, 3H, OCH.sub.2       CH.sub.3)                                                                      Example 16: 9.33(d, 1H, CHS); 4.24(m, 4H, OCH.sub.2 and NCH.sub.2);            3.40(m, 1H, SCH); 1.80(m, 2H, SCHCH.sub.2); 1.42(m, 9H, OCH.sub.2              CH.sub.3,                                                                      SCHCH.sub.3 and NCH.sub.2 CH.sub.3); 1.18(m, 3H, SCHOCH.sub.3)CH.sub.2         CH.sub.3                                                                       Example 17: 9.35(d, 1H, CHS); 5.30(dd, 2H, NCH.sub.2 SCH.sub.3); 4.38(m,       2H, OCH.sub.2); 3.40(m, 1H, SCH); 2.20(s, 3H, SCH.sub.3); 1.75(m, 2H,          SCHCH.sub.2); 1.40(m, 6H, OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.10(m,         3H,                                                                            SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                                Example 18: 9.35 (d, 1H, CHS); 4.30(m, 4H, OCH.sub.2 and NCH.sub.2);           2.40(d, 3H, SCH.sub.3); 1.40(m, 6H, OCH.sub.2 CH.sub.3 and NCH.sub.2           CH.sub.3)                                                                      Example 19: 9.30(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.50(d, 3H,              NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2);           1.50(t, 3H,                                                                    OCH.sub.2 CH.sub.3) 1.04 (m, 3H, SCH.sub.2 CH.sub.2 CH.sub.3)                  Example 20: 9.30(d, 1H, CHS); 4.38(m, 2H, OCH.sub.2); 3.60(m, 1H,              SCH), 3.35(d, 3H, NCH.sub.3); 1.42(t, 9H, OCH.sub.2 CH.sub.3 and               SCH(CH.sub.3).sub.2                                                            Example 21: 9.35(bd, 1H, CHS); 4.22(m, 2H, OCH.sub.2); 3.38(m, 1H,             SCH); 1.70(m, 2H, SCHCH.sub.2); 1.38(m, 6H, OCH.sub.2 CH.sub.3 and             SCHCH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3                       Example 22: 9.30(d, 1H, CHS); 4.20(m, 2H, OCH.sub.2); 3.40(d, 3H,              OCH.sub.3); 3.38(m, 1H, SCH); 1.80(m, 2H, SCHCH.sub.2); 1.45(m, 6H,            OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2         CH.sub.3)                                                                      Example 23: 9.35(d, 1H, CHS); 6.00(m, 1H, NCH.sub.2 CH═CH.sub.2);          5.40(m, 2H, NCH.sub.2 CH═CH.sub.2); 4.38(m, 4H, DNCH.sub.2 and             OCH.sub.2);                                                                    3.38(m, 1H, SCH); 1.80(m, 2H, SCHCH.sub.2); 1.50(m, 6H,                        OCH.sub.2 CH.sub. 3 and SCHCH.sub.3); 1.05(m, 3H,                              SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                                Example 24: 9.30(d, 1H, CHS); 4.36(m, 2H, OCH.sub.2); 3.42(d, 3H,              NCH.sub.3); 1.58(d, 9H, SC(CH.sub.3).sub.3 ; 1.42(t, 3H, OCH.sub.2             CH.sub.3)                                                                 

                  TABLE III (cont.)                                                ______________________________________                                         Nuclear Magnetic Resonance Data (ppm, δ)                                 ______________________________________                                         Example 25: 9.35(d, 1H, CHS); 4.36(m, 2H, OCH.sub.2); 3.38(d, 3H,              NCH.sub.3); 3.28(m, 1H, SCH); 1.78(m, 4H, SCH(CH.sub.2 CH.sub.3).sub.2 ;       1.40(t, 3H,                                                                    OCH.sub.2 CH.sub.3); 1.00(m, 6H, SCH(CH.sub.2 CH.sub.3).sub.2                  Example 26: 9.30(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.40(d, 3H,              NCH.sub.3); 3.38(m, 1H, SCH); 1.78(m, 2H, SCHCH.sub.2); 1.50(t, 6H,            OCH.sub.2 CH.sub.3) and SCHCH.sub.3); 1.05(m, 3H, SCH(CH.sub.3)CH.sub.2        CH.sub.3)                                                                      Example 27: 9.35(d, 1H, CHS); 4.35(m, 2H, OCH.sub.2); 3.90(m, 2H,              NCH.sub.2); 3.38(m, 1H, SCH); 1.78(m, 4H, SCHCH.sub.2 and                      NCH.sub.2 CH.sub.2); 1.40(m, 6H, OCH.sub.2 CH.sub.3 and SCHCH.sub.3);          1.00(m, 6H,                                                                    NCH.sub.2 CH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.3)                Example 28: Not Available                                                      Example 29: 9.30(d, 1H, CHS); 7.10(m, 5H, aromatic); 5.00(m, 2H,               NCH.sub.2); 4.00(m, 2H, OCH.sub.2); 3.38(m, 1H, SCH);                          1.78(m, 2H, SCHCH.sub.2): 1.50(t, 6H, OCH.sub.2 CH.sub.3 and                   SCHCH.sub.3);                                                                  1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 30: 9.30(d, 1H, CHS); 5.10(d, 2H, NCH.sub.2); 4.38(m, 2H,              OCH.sub.2); 3.40(m, 1H, SCH); 2.50(S, 3H, NCH.sub.2 SCH.sub.3); 1.75(m,        2H,                                                                            SCHCH.sub.2); 100 (m, SCH(CH.sub.3)--H.sub.2 CH.sub.3)                         Example 31: 9.35(d, 1H, CHS); 4.30(m, 2H, OCH.sub.2); 3.36(d, 3H,              NCH.sub.3); 2.90(m, 2H, SCH.sub.2); 1.38(dt, 6H, OCH.sub.2 CH.sub.3 and        SCH.sub.2 CH.sub.3)                                                            Example 32: 9.35(d, 1H, CHS); 4.35(m, 2H, OCH.sub.2); 3.35(d, 3H,              NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2);           1.50(t, 3H,                                                                    OCH.sub.2 CH.sub.3); 1.02(t, 3H, SCH.sub.2 CH.sub.2 CH.sub.3)                  Example 33: 9.30(d, 1H, CHS); 4.38(m, 2H, OCH.sub.2); 3.50(m, 1H,              CSCH); 3.36(d, 3H, NCH.sub.3); 1.50(t, 9H, OCH.sub.2 CH.sub.3 and              SCH(CH.sub.3).sub.2)                                                           Example 34: 9.38(d, 1H, CHS); 6.10(m, 1H, NCH.sub.2 CH═CH.sub.2);          5.48(m, 2H, NCH.sub.2 CH═CH.sub.2); 4.78(m, 2H, SCH.sub.2); 4.40(m,        2H,                                                                            OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m, 2H, SCHCH.sub.2); 1.40(m, 6H,            OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2         CH.sub.3)                                                                      Example 35: 9.40(d, 1H, CHS); 4.35(m, 2H, OCH.sub.2); 3.38(m, 1H,              SCH); 3.30(d, 3H, NCH.sub.3); 1.75(m, 4H, SCH(CH.sub.2 CH.sub.3); 1.50(t,      3H,                                                                            OCH.sub.2 CH.sub.3); 1.10(m, 6H, SCH(CH.sub.2 CH.sub.3).sub.2                  Example 36: 9.30(d, 1H, CHS); 4.30(m, 4H, OCH.sub.2 and NCH.sub.2);            3.40(m, 1H, SCH); 1.80(m, 4H, SCH(CH.sub.2 CH.sub.3).sub.2 ; 1.50(t, 3H,       OCH.sub.2 CH.sub.3); 1.08(m, 6H, SCH(CH.sub.2 CH.sub.3).sub.2                  Example 37: 8.90(S, 1H, OCH); 6.00(m, 1H, NCH.sub.2 CH═CH.sub.2);          5.40(m, 2H, NCH.sub.2 CH═CH.sub.2); 4.38(m, 4H, OCH.sub.2,                 NCH.sub.2); 3.42(m,                                                            1H, SCH) 1.78(m, 2H, SCHCH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and          SCHCH.sub.3); 1.02(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                      Example 38: 8.85(S, 1H, CCH); 4.40(dd, 2H, NCH.sub.2 CHCH);                    4.38(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 2.38(t, 1H, NCH.sub.2 CHCH);         1.80(m, 2H, SCHCH.sub.2) 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                    SCHCH.sub.3);                                                                  1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 39: 8.9(S, 1H, CCH); 4.80(d, 2H, NCH.sub.2); 3.30(m, 2H,               OCH.sub.2); 3.38(m, 1H, SCH) 2.30(S, 3H, NCH.sub.2 SCH.sub.3); 1.78(m,         2H,                                                                            SCHCH.sub.2); 1.50 (m, 6H, OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.02(m,        3H,                                                                            SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                                Example 44: 8.90(s, 1H, COH); 3.50(m, 3H, OCH.sub.2, SCH); 3.00 (m,            2H, NCH.sub.2); 1.78(m, 2H, SCHC .sub.--H.sub.2); 1,50(m, 10H, OCH.sub.2       CH.sub.3,                                                                      SCHCH.sub.3 and NCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3); 1.00(m, 6H,             SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                 and NCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).                                     Example 45: 8.70(d, 1H, COH); 8.65 (s, NHCHO); 4.20(m, 2H,                     OCH.sub.2); 3.38(m, 1H, SCH); 1.78(m, 2H, SCHCH.sub.2); 1.50(m, 6H,            OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.02(m, 3H, SCH(CH.sub.3)CH.sub.2         CH.sub.3).                                                                     Example 46: 8.70(s, 1H, COH); 4.68(d, 2H, NCH.sub.2 CN); 4.48(m, 2H,           OCH.sub.2); 3.42(m, 1H, SCH); 1.78(m, 2H, SCHCH.sub.2); 1.50(m, 6H,            OCH.sub.2 CH.sub.3 and SCHCH.sub.3); 1.02(m, 3H, SCH(CH.sub.3)CH.sub.2         CH.sub.3).                                                                     Example 49: 8.68(S, 1H, COH); 4.30(m, 2H, OCH.sub.2); 3.10(d, 3H,              NCH.sub.3); 2.80(m, 2H, SCH.sub.2); 1.98(m, 1H, SCH.sub.2 CH); 1.48(t,         3H,                                                                            OCH.sub.2 CH.sub.3); 1.00 (d, 6H, SCH.sub.2 CH(CH.sub.3).sub.2).               Example 50: 8.70(s, 1H, COH); 4.40(m, 2H, OCH.sub.2); 3.10(d, 3H,              NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.55(m, 7H, OCH.sub.2 CH.sub.3 and         SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3); 1.00(m, 3H, SCH.sub.2 CH.sub.2          CH.sub.2 CH.sub.3).                                                            Example 51: 8.70(s, 1H, COH); 4.38(m, 2H, OCH.sub.2); 3.10(d, 3H,              NCH.sub.3); 3.05(m, 2H, SCH.sub.2); 1.70(m, 6H, OCH.sub.2 CH.sub.3 and         SCH.sub.2 CH.sub.2 CH); 1.10(d, 6H, SCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2.     Example 52: 8.80(s, 1H, COH); 4.38(m, 2H, OCH.sub.2); 3.10(d, 3H,              NCH.sub.3); 3.00(m, 2H, SCH.sub. 2); 1.70(m, 6H, OCH.sub.2 CH.sub.3 and        SCH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3); 1.00(m, 6H,                          SCH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3).                                      Example 53: 8.75(s, 1H, COH); 4.38(m, 2H, OCH.sub.2); 3.30(m, 1H,              SCH); 3.10 (d, 3H, NCH.sub.3); 1.78(m, 2H, SCHCH.sub.2); 1.50(m, 8H,           OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.2); 1.00(m, 3H,            SCH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3).                                      Example 54: 8.70(s, 1H, COH); 590(m, 1H, SCH.sub.2 CH.sub.2 CH═CH.sub.     2);                                                                            5.20(m, 2H, SCH.sub.2 CH.sub.2 CH═CH.sub.2); 4.38(m, 2H, OCH.sub.2);       3.20(d,                                                                        3H, NCH.sub.3); 3.10(m, 2H, SCH.sub.2 CH.sub.3); 2.60(m, 2H, SCH.sub.2);       1.50(t, 3H, OCH.sub.2 CH.sub.3).                                          

                  TABLE III (cont.)                                                ______________________________________                                         Nuclear Magnetic Resonance Data (ppm, δ)                                 ______________________________________                                         Example 55: 8.75(s, 1H, COH); 4.40(m, 2H, OCH.sub.2); 3.70(m, 2H,              SCH.sub.2 CH.sub.2 OCH.sub.3); 3.40(s, 3H, SCH.sub.2 CH.sub.2 OCH.sub.3),      3.20(d, 3H,                                                                    NCH.sub.3); 3.15(m, 2H, SCH.sub.2); 1.50(t, 3H, OCH.sub.2 CH.sub.3).           Example 56: 8.75(s, 1H, COH); 4.40(m, 2H, OCH.sub.2); 3.60(m, 1H,              SCH); 3.00 (d, 3H, NCH.sub.3); 1.78(m, 2H, SCHCH.sub.2); 1.50(m,               3H, SCHCH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3).                 Example 57: 8.80(s, 1H, COH); 4.40(m, 2H, OCH.sub.2); 3.70(m, 3H,              NCH.sub.2 and SCH); 1.60(m, 7H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.2            CH.sub.3).sub.2 ;                                                              1.00(m, 6H, SCH(CH.sub.2 CH.sub.3).sub.2.                                      Example 58: 8.75(s, 1H, COH); 4.40(m, 2H, OCH.sub.2); 3.60(m, 2H,              NCH.sub.2); 2.98(m, 2H, SCH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2);           1.40(m, 6H,                                                                    NCH.sub.2 CH.sub.3 and OCH.sub.2 CH.sub.3); 1.00(m, 3H, SCH.sub.2              CH.sub.2 CH.sub.3)                                                             Example 59: 8.75(d, 1H, COH); 8.70(s, 1H, NHCHO); 4.40(m, 2H,                  OCH.sub.2); 3.00(m, 2H, SCH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2);           1.50(m, 3H,                                                                    OCH.sub.2 CH.sub.3); 1.10 (m, 3H, SCH.sub.2 CH.sub.2 CH.sub.3)                 Example 60: 8.70(s, 1H, COH); 4.20(m, 2H, OCH.sub.2); 3.65(m, 2H,              NCH.sub.2); 4.40(m, 1H, SCH); 1.78(m, 4H, OCH.sub.2 CH.sub.2 and               SCH(CH.sub.3)CH.sub.2); 1.40(m, 6H, NCH.sub.2 CH.sub.3 and                     SCH(CH.sub.3)); 1.00(m,                                                        6H, OCH.sub.2 CH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.3)            Example 61: 8.70(s, 1H, COH); 4.30(m, 2H, OCH.sub.2); 3.50(m, 1H,              SCH); 3.20(d, 3H, NCH.sub.3); 1.80(m, 4H, OCH.sub.2 CH.sub.2 and               SCH(CH.sub.3)CH.sub.2); 1.50(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3);           1.00(m, 6H,                                                                    OCH.sub.2 CH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.3)                Example 62: 8.80(s, 1H, COH); 4.80(m, 2H, OCH.sub.2); 3.95(m, 2H,              NCH.sub.2); 3.58(m, 1H, SCH); 1.90(m, 2H, SCH(CH.sub.3)CH.sub.2);              1.62(m, 6H, NCH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.3 );           1.20(m, 3H,                                                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                                Example 63: 8.70(s, 1H, COH); 5.10(m, 2H, OCH.sub.2 CH.sub.2 F);               4.80(m, 2H,OCH.sub.2 CH.sub.2 F); 3.60(m, 1H, SCH); 3.10(d, 3H,                NCH.sub.3);                                                                    1.78(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.60(m, 3H, SCH(CH.sub.3)); 1.10(m,        3H,                                                                            SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                                Example 64: 8.80(s, 1H, COH); 4.38(m, 2H, OCH.sub.2 CH.sub.2 OCH.sub.3);       3.90(m, 2H, OCH.sub.2 CH.sub.2 OCH.sub.3); 3.60(s, 3H, OCH.sub.2 CH.sub.2      OCH.sub.3);                                                                    3.30(d, 3H, NCH.sub.3); 1.78(m, 2H, SCH(CH.sub.3)CH.sub.2 CH.sub.3);           1.50(m,                                                                        3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2         CH.sub.3)                                                                      Example 65: 8.75(s, 1H, COH); 7.00, 6.10 and 5.20(m, 1H,                       OCH.sub.2 CF.sub.2 CF.sub.2 H); 4.60(m, 2H, OCH.sub.2); 3.60(m, 1H, SCH);      3.20(d,                                                                        3H, NCH.sub.3); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2 CH.sub.3); 1.50(m, 3H,       SCH(CH.sub.3)CH.sub.2 CH.sub.3); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2             CH.sub.3)                                                                      Example 66: 9.30(d, 1H, CHS); 7.60(s, 4H, OC.sub.6 H.sub.4 -- 3CF.sub.3);      3.50(d,                                                                        3H, NCH.sub.3) 3.40(m, 1H, SCH); 1.78(m, 2H, SCH(CH.sub.3)CH.sub.2             CH.sub.3);                                                                     1.50(m, 3H, SCH(CH.sub.3)) 1.00 (m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)        Example 67: 9.35(d, 1H, CHS); 5.30(dd, 2H, NCH.sub.2 SCH.sub.3); 4.40(m,       2H, OCH.sub.2); 3.50(m, 1H, SCH); 2.40(s, 3H, NCH.sub.2 SCH.sub.3);            1.78(m,                                                                        2H, SCH(CH.sub.3)CH.sub.2); 1.60 (m, 6H, OCH.sub.2 CH.sub.3 and                SCH(CH.sub.3)CH.sub.2 CH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2             CH.sub.3)                                                                      Example 68: 9.30(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.50(d, 3H,              NCH.sub.3); 2.90 (dd, 2H, SCH.sub.2); 2.00(m, 1H, SCH.sub.2 CH); 1.50(t,       3H,                                                                            OCH.sub.2 CH.sub.3); 1.00(d, 6H, SCH.sub.2 CH(CH.sub.3).sub.2)                 Example 69: 9.35(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.50(d, 3H,              NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2);           1.58(m, 5H,                                                                    SCH.sub.2 CH.sub.2 CH.sub.2 and OCH.sub.2 CH.sub.3); 1.00(m, 3H,               SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3)                                          Example 70: 9.35(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.50(d, 3H,              NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 2.00(m, 1H, SCH.sub.2 CH.sub.2 CH);        1.60(m,                                                                        2H, SCH.sub.2 CH.sub.2); 1.45(t, 3H, OCH.sub.2 CH.sub.3); 1.00(d, 6H,          SCH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2)                                         Example 71: 9.30(d, 1H, CHS); 4.50(m, 2H, OCH.sub.2); 4.60(d, 3H,              NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.70(m, 9H, OCH.sub.2 CH.sub.3 and         SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3);                                1.00 (m, 3H, SCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3)                    Example 72: 9.30(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.50(d, 3H,              NCH.sub.3); 2.90(m, 2H, SCH.sub.2); 2.00(m, 1H, SCH.sub.2 CH(CH.sub.3));       1.50(m,                                                                        8H, OCH.sub.2 CH.sub.3 and SCH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3);           1.00(m,                                                                        3H, SCH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3)                                   Example 73: 9.35(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.55(m, 1H,              SCH); 3.50 (d, 3H, NCH.sub.3); 2.10(m, 2H, SCH(CH.sub.3)CH.sub.2);             1.60(m, 8H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.3 )CH.sub.2 CH.sub.2             CH.sub.3);                                                                     1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3)                           Example 74: 9.30(d, 1H, CHS); 6.00(m, 1H, SCH.sub.2 CH.sub.2 CH═CH.sub     .2);                                                                           5.30(m, 2H, SCH.sub.2 CH.sub.2 CH═CH.sub.2); 4.50(m, 2H, OCH.sub.2);       3.50(d,                                                                        3H, NCH.sub.3); 3.10(m, 2H, SCH.sub.2 CH.sub.2 CH═CH.sub.2); 2.65(m,       2H,                                                                            SCH.sub.2); 1.60(t, 3H, OCH.sub.2 CH.sub.3).                                   Example 75: 9.30(d, 1H, CHS); 4.40(m, 2H, OCH.sub.2); 3.60(m, 2H,              SCH.sub.2 CH.sub.2 OCH.sub.3); 3.45(s, 3H, SCH.sub.2 CH.sub.2 OCH.sub.3);      3.40(d, 3H,                                                                    NCH.sub.3); 3.00(m, 2H, SCH.sub.2); 1.45(t, 3H, OCH.sub.2 CH.sub.3)            Example 76: 9.30(d, 1H, CHS); 4.60(m, 2H, OCH.sub.2); 3.60(d,                  3H, NCH.sub.3); 3.62(m, 1H, SCH); 1.78(m, 2H, SCH(CH.sub.3)CH.sub.2);          1.50(m, 3H, SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)        Example 77: 9.30(d, 1H, CHS); 4.40(m, 4H, OCH.sub.2, NCH.sub.2);               3.50(m, 1H, SCH); 1.80(m, 4H, OCH.sub.2 CH.sub.2 and SCH(CH.sub.3)CH.sub.2     );                                                                             1.50(m, 6H, NCH.sub. 2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2 CH.sub.3);           1.10(m, 6H, OCH.sub.2 CH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2              CH.sub.3)                                                                      Example 78: 9.30(d, 1H, CHS); 4.30(m, 2H, OCH.sub.2); 3.50(d, 3H,              NCH.sub.3); 3.50(m, 1H, SCH); 1.80(m, 4H, SCH(CH.sub.3)CH.sub.2 and            OCH.sub.2 CH.sub.2); 1.50(t, 3H, SCH(CH.sub.3)); 1.00(m, 6H,                   SCH(CH.sub.3)CH.sub.2 CH.sub.3 and OCH.sub.2 CH.sub.2 CH.sub.3)           

                  TABLE III (cont.)                                                ______________________________________                                         Nuclear Magnetic Resonance Data (ppm, δ)                                 ______________________________________                                         Example 79: 9.30(d, 1H, CHS); 4.90(d, 2H, NCH.sub.2); 4.40(m, 2H,              OCH.sub.2); 3.80(s, 3H, NCH.sub.2 CO.sub.2 CH.sub.3); 3.50(m, 1H, SCH);        1.80(m,                                                                        2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                 SCH(CH.sub.3)CH.sub.2 CH.sub.3); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2             CH.sub.3)                                                                      Example 80: 9.28(d, 1H, CHS); 7.40(m, 5H, NCH.sub.2 C.sub.6 H.sub.5);          5.65(m, 2H,                                                                    NCH.sub.2); 4.30(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,              SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                     SCH(CH.sub.3)CH.sub.2);                                                        1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 81: 9.30(d, 1H, CHS); 7.40(m, 4H, NCH.sub.2 C.sub.6 H.sub.4 F);        5.50(m,                                                                        2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m,              2H, SCH(CH.sub.3)CH.sub.2); 1.50 (m, 6H, OCH.sub.2 CH.sub.3 and                SCH(CH.sub.3)CH.sub.2); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)            Example 82: 9.30(d, 1H, CHS); 7.20(m, 4H, NCH.sub. 2 C.sub.6 H.sub.4           OCH.sub.3); 5.40                                                               (m, 2H, NCH.sub.2); 4.30 (m, 2H, OCH.sub.2); 3.98(s, 3H, NCH.sub.2             C.sub.6 H.sub.4 OCH.sub.3);                                                    3.30(m, 1H, SCH); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H,              OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)CH.sub.2); 1.00 (m, 3H,                    SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                                Example 83: 9.30(d, 1H, CHS); 7.60(m, 4H, NCH.sub.2 C.sub.6 H.sub.4            CF.sub.3);                                                                     5.70(m, 2H, NCH); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m,            2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                 SCH(CH.sub.3)CH.sub.2); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)            Example 84: 9.25(d, 1H, CHS); 4.50(d, 2H, NCH.sub.2); 4.40(m, 2H,              OCH.sub.2); 3.70(t, 2H, NCH.sub.2 CH.sub.2 CH.sub.2 Cl); 3.38(m, 1H,           SCH); 2.40(m, 2H,                                                              NCH.sub.2 CH.sub.2); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H,           OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2       CH.sub.3)                                                                      Example 85: 9.30(d, 1H, CHS); 7.50(m, 4H, NCH.sub.2 SC.sub.6 H.sub.4           Cl);                                                                           4.40(m, 2H, OCH.sub.2); 3.60(m, 1H, SCH); 1.80(m, 2H,                          SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                     SCH(CH.sub.3));                                                                1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 86: 9.30(d, 1H, CHS); 5.60(m, 2H, NCH.sub.2 C(Br)═CH.sub.2);       5.00(NCH.sub.2); 4.50(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,         SCH(CH.sub.3)CH.sub.2); 1.50 (m, 6H, OCH.sub.2 CH.sub.3 and                    SCH(CH.sub.3)CH.sub.2);                                                        1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 87: 9.30(d, 1H, CHS); 7.40(m, 5H, NCH.sub.2 CH═CHC.sub.6           H.sub.5);                                                                      6.60(m, 2H, CH.sub.2 CH═CH); 5.00(m, 2H, NCH.sub.2); 4.30(m, 2H,           OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);              1.50(m, 6H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.00(m,                     3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                            Example 88: 9.30(d, 1H, CHS); 5.00(d, 2H, NCH.sub.2); 4.60(m, 4H,              OCH.sub.2 and NCH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3); 3.60(m, 1H, SCH);         1.80(m,                                                                        2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 9H, OCH.sub.2 CH.sub.3, NCH.sub. 2         CO.sub.2 CH.sub.2 CH.sub.3                                                     and SCH(CH.sub.3); 1.20(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                 Example 89: 9.30(d, 1H, CHS); 4.38(m, 2H, OCH.sub.2 CH.sub.2); 3.60(m,         2H, OCH.sub.2 CH.sub.2 OCH.sub.3); 3.39(d, 3H, NCH.sub.3); 3.38(s, 3H,         OCH.sub.3);                                                                    3.38(m, 1H, SCH); 1.80 (m, 2H, SCH(CH.sub.3)CH.sub.2); 1.38(t, 3H,             SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 90: 9.35(d, 1H, CHS); 7.00, 6.00 and 5.20(m, 1H,                       HCF.sub.2 CH.sub.2); 4.58 (m, 2H, OCH.sub.2 CF.sub.2 CF.sub.2 H); 3.50(m,      1H, SCH);                                                                      3.50(d, 3H, NCH.sub.3); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.50(t, 3H,        SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 91: 9.35(d, 1H, CHS); 4.60(m, 2H, OCH.sub.2 CF.sub.3); 3.60(m,         1H,                                                                            SCH); 3.60(m, 2H, NCH.sub.2); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);              1.60(m,                                                                        3H, SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                Example 92: 9.30(d, 1H, CHS); 7.40(m, 5H, NCH.sub.2 SC.sub.6 H.sub.5);         5.60(d,                                                                        2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.60(m, 1H, SCH); 1.80(m,              2H, SCH(CH.sub.3)CH.sub.2); 1.60(m, 3H, OCH.sub.2 CH.sub.3,                    SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 93: 9.30(d, 1H, CHS); 5.98(m, 2H, NCH.sub.2 CH═CHCH.sub.3);        4.90 (m, 2H OCH.sub.2); 4.60(m, 2H, NCH.sub.2); 3.50(m, 1H, SCH);              1.90(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.80(m, 3H, NCH.sub.2 CH═CHCH.sub.     3);                                                                            1.60(m, 3H, OCH.sub.2 CH.sub.3, SCH(CH.sub.3)); 1.10(m, 3H,                    SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                                Example 94: (d, 1H, CHS); 7.80(m, 4H, NCH.sub.2 C.sub.6 H.sub.4); 5.40(m,      2H,                                                                            NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.30(m, 1H, SCH); 1.80(m, 2H,              SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                     SCH(CH.sub.3));                                                                1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 121: 8.90(s, 1H, CHO); 4.40(d, 2H, NCH.sub.2); 4.38(m, 2H,             OCH.sub.2); 3.85(s, 3H, NCH.sub.2 CO.sub.2 CH.sub.3); 3.50(m, 1H, SCH);        1.80(m, 2H,                                                                    SCH(CH.sub.3)CH.sub.2); 1.60(m, 9H, OCH.sub.3, OCH.sub.2 CH.sub.3,             SCH(CH.sub.3 ); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 122: 8.85(s, 1H, CHO); 7.50(m, 5H, NCH.sub.2 CH.sub.6 H.sub.5);        5.00(dd, 2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH);             1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.60(m, 6H, OCH.sub.3 and                  SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 123: 8.85(s, 1H, CHO); 7.40(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);         4.90(m,                                                                        2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,          SCH(CH.sub.3)CH.sub.2); 1.60(m, 6H, OCH.sub.3 and SCH(CH.sub.3)); 1.00         (m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                        Example 124: 8.90(s, 1H, CHO); 7.30(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);         5.00(dd, 2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.90(s, 3H, OCH.sub.3);       3.59(m, 1H, SCH); 1.80 (m, 2H, SCH(CH.sub.3)CH.sub.2); 1.55(m,                 6H, OCH.sub.3 and SCH(CH.sub.3)); 1.00(m, 3H,                                  SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                                Example 125: 8.85(s, 1H, CHO); 7.80(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);         5.00(dd,                                                                       2H, NCH.sub.2); 4.38(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,          SCH(CH.sub.3)CH.sub.2); 1.59(m, 6H, OCH.sub.3 and SCH(CH.sub.3)); 1.10(m,      3H,                                                                            SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                                Example 126: 8.90(s, 1H, CHO); 4.40(m, 2H, OCH.sub.2); 3.90(m, 2H,             NCH.sub.2); 3.80(m, 2H, NCH.sub.2 CH.sub.2 CH.sub.2 Cl); 3.409m, 1H,           SCH);                                                                          2.38(m, 2H, NCH.sub.2 CH.sub.2); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);           1.55(m, 6H,                                                                    OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.10 (m, 3H, SCH(CH.sub.3)CH.sub.2      CH.sub.3)                                                                      Example 127: 8.90(s, 1H, CHO); 7.40(m, 4H, NCH.sub.2 SC.sub.6 H.sub.4);        5.00(d,                                                                        2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 1.75(m, 2H,          SCH(CH.sub.3)CH.sub.2); 1.40(m, 6H, OCH.sub.2 CH.sub.3 and                     SCH(CH.sub.3));                                                                1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 128: 8.90(s, 1H, CHO); 5.90(m, 2H, NCH.sub.2 C(BR)═CH.sub.2);      4.60(m, 2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH);              1.80(m, 2H, SCH(CH.sub.3) CH.sub.2); 1.55(m, 6H, OCH.sub.2 CH.sub.3 and        SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)               

                  TABLE III (cont.)                                                ______________________________________                                         Nuclear Magnetic Resonance Data (ppm, δ)                                 ______________________________________                                         Example 129: 8.90(s, 1H, CHO); 7.40(s, 5H, NCH.sub.2 CH═CHC.sub.6          H.sub.5);                                                                      6.80(d, 1H, NCH.sub.2 CH═CH); 6.40(m, 1H, NCH.sub.2 CH═CH);            4.60(m, 2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH);              1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.55(m, 6H, OCH.sub.2 CH.sub.3             and SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                Example 130: 8.90(s, 1H, CHO); 4.40(d, 2H, NCH.sub.2); 4.38(m, 4H,             OCH.sub.2 and NCH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3); 3.50(m, 1H, SCH);         1.80(m, 2H,                                                                    SCH(CH.sub.3)CH.sub.2); 1.55 (m, 9H, OCH.sub.2 CH.sub.3, NCH.sub.2             CO.sub.2 CH.sub.2 CH.sub.3                                                     and SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3) CH.sub.2 CH.sub.3)               Example 131: 8.85(s, 1H, CHO); 8.00(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);         5.00(d,                                                                        2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.45(m, 1H, SCH); 1.80(m,              2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                 SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 132: 8.90(s, 1H, CHO); 7.80(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);         5.00(dd,                                                                       2H, NCH.sub.2); 3.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,          SCH(CH.sub.3) CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                    SCH(CH.sub.3));                                                                1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 133: 8.90(s, 1H, CHO); 8.00(m, 5H, NCH.sub.2 COC.sub.6 H.sub.5);       5.20(d, 2H, NCH.sub.2); 3.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH);              1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.55(m, 6H, OCHCH.sub.2 CH.sub.3 and       SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 134: 8.90(s, 1H, CHO); 7.50(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);         5.00(d, 2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH),              1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and         SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 135: 8.90(s, 1H, CHO); 7.30(m, 4H, NCH.sub.2 OC.sub.6 H.sub.4);        5.70(d, 2H, NCH.sub.2); 4.30(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH);              1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.55(m, 6H, OCH.sub.2 CH.sub.3 and         SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 136: 8.90(s, 1H, CHO); 7.78(m, 7H, NCH.sub.2 C.sub.10 H.sub.7);        5.10(dd, 2H, NCH.sub.2); 4.00(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH);             1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.60(m, 6H, OCH.sub.2 CH.sub.3 and         SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 137: 8.90(s, 1H, CHO); 5.80(m, 2H, NCH.sub.2 CH═CHCH.sub.3);       4.40(m, 4H, OCH.sub.2 and NCH.sub.2); 3.40(m, 1H, SCH);                        1.90(m, 5H, SCH(CH.sub.3) and NCH.sub.2 CH═CHCH.sub.3 ; 1.50(m,            6H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub     .2 CH.sub.3)                                                                   Example 138: 8.90(s, 1H, CHO); 7.48(m, 3H, NCH.sub.2 C.sub.6 H.sub.3);         5.30(dd,                                                                       2H, NCH.sub.2); 4.30(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,          SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                     SCH(CH.sub.3));                                                                1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 139: 8.85(s, 1H, CHO); 5.10(d, 2H, NCH.sub.2); 4.40(m, 2H,             OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);              1.50(m,                                                                        6H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.3); 1.10(m, 3H, SCH(CH.sub.3)CH.sub.     2 CH.sub.3)                                                                    Example 140: 8.90(s, 1H, CHO); 4.40(m, 2H, OCH.sub.2); 3.50(m, 2H,             NCH.sub.2); 2.75(m, 2H, SCH.sub.2); 1.50(m, 9H, NCH.sub.2 CH.sub.2             CH.sub.2 CH.sub.3,                                                             OCH.sub.2 CH.sub.3 and SCH.sub.2 CH.sub.2 CH.sub.3);                           1.00(m, 6H, SCH.sub.2 CH.sub.2 CH.sub.3 and NCH.sub.2 CH.sub.2 CH.sub.2        CH.sub.3)                                                                      Example 141: 8.90(s, 1H, CHO); 7.39(m, 5H, NCH.sub.2 C.sub.6 H.sub.5);         4.80(m,                                                                        2H, NCH.sub.2); 4.00(m, 2H, OCH.sub.2); 2.70(m, 2H, SCH.sub.2); 1.70(m,        2H,                                                                            SCH.sub.2 CH.sub.2); 1.20(m, 6H, SCH.sub.2 CH.sub.2 CH.sub.3 and               OCH.sub.2 CH.sub.3)                                                            Example 142: 8.90(s, 1H, CHO); 4.40(m, 6H, NCH.sub.2, OCH.sub.2,               NCH.sub.2 CO.sub.2 CH.sub.2); 3.00(m, 2H, SCH.sub.2); 1.70(m, 2H,              SCH.sub.2 CH.sub.2); 1.20(m, 9H, SCH.sub.2 CH.sub.2 CH.sub.3, OCH.sub.2        CH.sub.3                                                                       and NCH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3)                                      Example 143: 8.85(s, 1H, CHO); 4.60(m, 4H, OCH.sub.2 and NCH.sub.2);           3.90(m, 2H, NCH.sub.2 CH.sub.2 CH.sub.2 Cl); 3.10(m, 2H, SCH.sub.2);           2.20(m, 2H,                                                                    NCH.sub.2 CH.sub.2); 1.80(m, 2H, SCH.sub.2 CH.sub.2); 1.50(m, 3H,              OCH.sub.2 CH.sub.3); 1.00(m, 3H, SCH.sub.2 CH.sub.2 CH.sub.2)                  Example 144: 8.90(s, 1H, CHO); 7.80(m, 9H,                                     NCH.sub.2 C.sub.6 H.sub.4 OCH.sub.2 C.sub.6 H.sub.5); 5.30(s, 2H,              NCH.sub.2 C.sub.6 H.sub.4 OCH.sub.2);                                          5.00(m, 2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH);              1.80(m, 2H, SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and         SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 146: 8.90(s, 1H, CHO); 5.10(m, 2H, NCH.sub.2 C(CH.sub.3)═CH.su     b.2);                                                                          4.30 (m, 4H, OCH.sub.2 and NCH.sub.2); 3.50(m, 1H, SCH); 1.80(s, 3H,           NCH.sub.2 C(CH.sub.3)═CH.sub.2); 1.45(m, 6H, OCH.sub.2 CH.sub. 3 and       SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 148: 8.90(s, 1H, CHO); 7.50(s, 5H, NCH.sub.2 C.sub.6 H.sub.5);         5.00(dd,                                                                       2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m, 2H,          SCH(CH.sub.3) CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                    SCH(CH.sub.3)); 1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                    Example 152: 8.90(s, 1H, CHO); 7.38(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);         4.78(m,                                                                        2H, NCH.sub.2); 4.20(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m, 2H,          SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                     SCH(CH.sub.3));                                                                1.00(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 159: 8.85(s, 1H, CHO); 8.00(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);         4.90(dd,                                                                       2H, NCH.sub.2); 4.30(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 1.80(m, 2H,          SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                     SCH(CH.sub.3));                                                                1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    Example 165: 8.90(s, 1H, CHO); 5.00(m, 2H, NCH.sub.2); 4.38(m, 2H,             OCH.sub.2 ); 3.50(m, 1H, SCH); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);             1.50(m,                                                                        6H, OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.10(m, 3H, SCH(CH.sub.3)CH.sub     .2 CH.sub.3                                                                    Example 176: 8.90(s, 1H, CHO); 8.00(m, 3H, NCH.sub.2 C.sub.6 H.sub.3);         4.90(dd,                                                                       2H, NCH.sub.2); 4.40(m, 2H, OCH.sub.2); 3.40(m, 1H, SCH); 2.70(s, 3H,          NCH.sub.2 C.sub.6 H.sub.3 CH.sub.3); 1.80(m, 2H, SCH(CH.sub.3)CH.sub.2);       1.50(m, 6H,                                                                    OCH.sub.2 CH.sub.3 and SCH(CH.sub.3)); 1.10 (m, 3H, SCH(CH.sub.3)CH.sub.2      CH.sub.3)                                                                      Example 180: 8.85(s, 1H, CHO); 7.70(m, 4H, NCH.sub.2 C.sub.6 H.sub.4);         4.90(dd,                                                                       2H, NCH.sub.2); 4.39(m, 2H, OCH.sub.2); 3.50(m, 1H, SCH); 1.80(m, 2H,          SCH(CH.sub.3)CH.sub.2); 1.50(m, 6H, OCH.sub.2 CH.sub.3 and                     SCH(CH.sub.3));                                                                1.10(m, 3H, SCH(CH.sub.3)CH.sub.2 CH.sub.3)                                    ______________________________________                                    

Table IV which follows sets forth the biological data obtained as described above for the exemplary compounds described in Table I.

    ______________________________________                                         Code Symbol                                                                              Common Name       Latin Name                                         ______________________________________                                         TSM       Two-spotted spider mite                                                                          Tetranychus                                                                    urticae                                            GPA       Green peach aphid Myzus persicae                                     CRW       Southern corn rootworm                                                                           Diabrotica un-                                                                 decimpunctata                                                                  howardi                                            NEMA      Southern root-knot nematode                                                                      Meloidogyne                                                                    incognita                                          ______________________________________                                    

A test solution containing 600 ppm of test compound in a solvent (acetone:methanol, 1:1) and then adding water to give an acetone:methanol:water system of 5:5:90. A test solution containing 150 ppm of test compound is prepared by diluting 1 part of 600 ppm test solution with three parts of water. A 1:1 mixture of alkylarlpolyetheralcohol (commercially available under the trademark TRITON® X-155) and a modified phthalic glycerol alkyl resin (commercially available under the trademark TRITON® B-1956) is utilized at the equivalent of one ounce per 100 gallons of test solution as a surfactant.

For the mite test, infested bean (Phaseolus limeanus) leaf section (˜1×1 inches) containing about 50 mites are placed in a Petri dish lid on a moistened piece of cotton. The leaves are then sprayed with the 600 ppm test solution using a rotating turntable. They are held for 24 hours and then the percent kill is determined.

For the aphid test, infected broccoli (Brassica oleracea) leaf section (˜1×1 inches) containing about 30 adult and mymphal aphids are placed in a Petri dish lid on a moistened piece of cotton. The leaves are then sprayed with the 600 ppm test solution using a rotating turntable. They are held for 24 hours and then the percent kill is determined.

For the rootworm larvae test, ten milliliters of the 150 ppm test solution are added to 200 milliliter of soil in a 16 oz. jar to give a concentration by volume of about 8 ppm. The jar is shaken to insure thorough mixing, immediately uncapped, and allowed to ai for 2 hours. Two presoaked kernels of Golden Cross Bantam corn (Zea map) are placed in the bottom of a 1 oz. plastic cap and covered with about 30 grams of treated soil. The soil surface is inoculated with approximately 120 southern corn rootworm eggs and the plastic cup closed iwth a tight-fitting cap. The test cup is held for 10 days at 27° C. and then the percent kill relative to the untreated check is determined.

For the nematode test, soil is homogenously inoculated with nematode eggs at the rate of about 5000 eggs per 200 milliliters of soil extracted from a macerated blend of tomato roots heavily knotted with the root knot nematode. Ten milliliters of the 150 ppm test solution are added to 200 milliliters of the inoculated soil in a 16 oz. jar to give a concentration by volume of about 8 ppm. The jar is shaken to insure thorough mixing, immediatley uncapped, and allowed to air for 24 hours. The soil is then placed into a 3-inch plastic pot after which time 3 cucumber (Cucumis sativus) seeds are planted. About 23 days thereafter, the cucumber plants are removed from the soil and root system examined for the presence of knots. A total of 25 knots or less is considered as a measure of control. Excellent control is characterized by 0-2 knots.

                  TABLE IV                                                         ______________________________________                                         Pesticidal Activity % Control.sup.a                                                    Soil Application                                                                               Foliar Application                                             (150 ppm)       (600 ppm)                                              Example   CRW     NEMA          TSM  GPA                                       ______________________________________                                          1        100     +++++         100   98                                        2        100     --            100   50                                        3        100     --             0    0                                         4         62     --             0    0                                         5         65     +++++         100  100                                        6        100     +++++         100  100                                        7        100     +++++         100  100                                        8         27     +++++          0    0                                         9        100     +++           100   95                                        10       100     --            100  NA                                         11       100     --            100  100                                        12        98     +++++          81   0                                         13       100     --            100  100                                        14       100     ++++          100  100                                        15        0      --             84   0                                         16       100     --            100  100                                        17                                                                             18       100     ++++          100   73                                        19                                                                             20                                                                             21        22     --             0    0                                         22       100     +++++         100  100                                        23       100     +++++         100   0                                         24       100     +++++         100   0                                         25       100     +++++         100  100                                        26       100     +++           100  100                                        27       100     +++++         100  100                                        28       100     +++++         100  100                                        29       100     +++++         100  100                                        30       100     +++++         100  100                                        31       100     ++++          100  100                                        32       100     +++++         100  100                                        33       100     +++++         100  100                                        34       100     +++           100  100                                        35       100     +++++         100  100                                        36       100     NA            100  100                                        37       100     +++++         100  100                                        38       100     +++++         100  100                                        39       100     +++++         100  100                                        40       100     --            100   95                                        41       100     +++++         100  100                                        42       100     +++++         100  100                                        43                                                                             44       100     +++++         100  100                                        45       100     --             89  100                                        46       100     +++++         100  100                                        47       100     +++++         100  100                                        48       100     +++++         100  100                                        49       100     +++           100  100                                        50       100     --            100   76                                        51        97     NA            NA   NA                                         52       100     +++           100   0                                         53       100     ++++          100   0                                         54        96     --            100   29                                        55       100     --            100  NA                                         56       100     +++++         100  NA                                         57       100     --            100  100                                        58       100     +++           100  100                                        59       100     --            100   40                                        60       100     --             0   100                                        61       100     ++             59  100                                        62       100     --             97   0                                         63       100     NA            100  100                                        64        94     --            100  100                                        65       100     +++++         100   83                                        66       100     --            100  100                                        67       100     ++++          100   73                                        68       100     +++           100  100                                        69       100     --            100   11                                        70       100     --            100   0                                         71        83     --            100   93                                        72       100     --            100  100                                        73       100     --            100  100                                        74        70     --            100  100                                        75       100     --            100  100                                        76       100     ++++          100  100                                        77       100     --             0   100                                        78       100     --             51  100                                        79        99     NA            100  100                                        80       100     ++            100  100                                        81       100     --            100  100                                        82       100     --            100  100                                        83       100     ++            100  100                                        84       100     --            100  100                                        85       100     --            100  100                                         86      100     --            100  100                                        87       100     +++           100  100                                        88       100     +++           100  100                                        89        82     +++++         100  100                                        90       100     +++++         100  100                                        91       100     +++++          33   0                                         92       100     --            100  100                                        93       100     --            100  100                                        94        99     --            100  100                                        95       100     +++++         100  100                                        96       100     --            100  100                                        97       100     --            100  100                                        98       100     +++++         100  100                                        99        89     +++++         100   91                                       100       100     ++++          100  100                                       101       100     --            100  100                                       102       100     +++++         100  100                                       103       100     --            100  100                                       104       100     ++++          100  100                                       105       100     ++++          100  100                                       106       100     +++           100  100                                       107       100     +++++         100  100                                       108       100     +++++         100  100                                       109       100     +++++         100  100                                       110        97     --            100  100                                       111        99     ++++          100  100                                       112       100     +++           100  100                                       113       100     +++++         100  100                                       114       100     +++++         100  100                                       115       100     +++++         100  100                                       116        98     +++++         100  100                                       117       100     +++           100  100                                       118       100     --            100  100                                       119        95     +++           100  100                                       120        90     --            100  100                                       121        98     +++++         100  100                                       122       100     ++++          100  100                                       123       100     ++            100  100                                       124       100     --            100  100                                       125       100     --            100  100                                       126       100     --            100  100                                       127       100     --            100  100                                       128       100     +++           100  NA                                        129       100     --            100  100                                       130       100     --            100  100                                       131       100     --            100  100                                       132       100     --            100  100                                       133       100     --            100  100                                       134       100     --            100  100                                       135       100     --            100  100                                       136       100     --            100  100                                       137       100     --            100   95                                       138       100     --            100  100                                       139       100     --            100  100                                       140       100     ++            100  100                                       141       100     --            100  100                                       142       100     ++++          100  100                                       143       100     ++            100  100                                       144        98     --            100  100                                       145       100     --            100  100                                       146       100     ++            100  100                                       147       100                   100  100                                       148       100                   100  100                                       149       100     +++           100  100                                       150       100     +++++         100  100                                       151       100     +++++         100  100                                       152       100     +++++         100  100                                       153       100     +++++         100  100                                       154       100     +++++         100  100                                       155       100     ++++          100  100                                       156       100     +++++         100  100                                       157       100     +++++         100  100                                       158       100     +++++         100  100                                       159        99     + +++         100  100                                       160       100     +++++         100  100                                       161        98     +++++         100  100                                       162        98     +++++         100  100                                       163       100     +++++         100  100                                       164       100     +++++         100  100                                       165       100     +++++         100  100                                       166       100     +++           100  100                                       167       100     +++++         100  100                                       168       100     +++++         100  100                                       169       100     +++++         100  100                                       170       100                   100  100                                       171        94     +++++         100  100                                       172        98     +++++         100  100                                       173       100     +++++         100  100                                       174       100     +++++         100  100                                       175       100     +++++         100  100                                       176        98     +++++         100  100                                       177       100     +++++         100  100                                       178       100     +++           100  100                                       179       100     +++++         NT   NT                                        180        0      +++++         100  100                                       ______________________________________                                         CRW =         Southern Corn Rootworm                                           NEMA =        Southern Root Knot Nematode                                      TSM =         Two Spotted Spider Mite                                          GPA =         Green Peach Aphid                                                NA =          Not Available                                                    ______________________________________                                                Rank    Knots                                                           ______________________________________                                                +++++   0-2                                                                    ++++    3-6                                                                    +++     7-9                                                                    ++      18-25                                                                  -       25+                                                             ______________________________________                                          .sup.a CRW, TSM, & GPA  Test results expressed as % control.                   NEMA  Test results expressed as rankings for degree of knotting.          

What is claimed is:
 1. A compound having the formula ##STR15## wherein: R¹ is unsubstituted or substituted (C₁ -C₄)alkyl wherein the substituent can be from one to four of the same or different bromo, chloro or fluoro groups;R² is unsubstituted straight or branched chain (C₂ -C₅)alkyl; R³ is hydrogen; R⁴ is unsubstituted or substituted (C₃ -C₆)alkenyl wherein the substituent can be from one to three of the same or different phenyl, alkyl, carbo(C₁ -C₄)alkoxy, bromo, chloro or fluoro groups; (C₃ -C₆)alkynyl; unsubstituted or substituted phenyl wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or dialkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent on the phenyl ring can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, benzyloxy, methylenedioxy, cyano, nitro, amino, or mono-- or dialkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; and Y and Z are O.
 2. A method of controlling arthropods which comprises applying directly to the arthropods or to the locus to be freed or protected from attack by arthropods an arthropodicidally effective amount of an active compound according to claim
 1. 3. A compound according to claim 1 wherein:R¹ is unsubstituted (C₁ -C₄)alkyl; R² is unsubstituted branched chain (C₂ -C₅)alkyl; R³ is hydrogen; and R⁴ is (C₃ -C₆)alkenyl; (C₃ -C₆)alkynyl; or unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent on the phenyl ring can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- and dialkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms and Y and Z are O.
 4. A compound according to claim 3 wherein:R¹ is unsubstituted straight or branched chain (C₂ -C₄)alkyl; R² is unsubstituted branched chain (C₂ -C₅)alkyl; R³ is hydrogen; and R⁴ is unsubstituted or substituted benzyl wherein the substituent on the phenyl ring can be from one to three of the same or different (C₁ -C₃)alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro or cyano.
 5. A compound according to claim 4 wherein:R¹ is ethyl; R² is unsubstituted branched chain (C₂ -C₅)alkyl; R³ is hydrogen; and R⁴ is substituted benzyl wherein the substituent on the phenyl ring can be from one to two of the same or different (C₁ -C₃)alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro or cyano.
 6. A compound according to claim 5 wherein:R¹ is ethyl; R² is 1-methylpropyl R³ is hydrogen; and R⁴ is 4-fluorobenzyl.
 7. A compound according to claim 5 wherein:R¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is 4-nitrobenzyl.
 8. A compound according to claim 5 wherein:R¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is 4-cyanobenzyl.
 9. A compound according to claim 5 whereinR¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is 4-trifluoromethylbenzyl.
 10. A compound according to claim 5 whereinR¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is 3-trifluoromethylbenzyl.
 11. An arthropodicide composition which comprises an arthropodicidally effective amount of a compound according to claim
 1. 12. An arthropodicide composition which comprises an arthropodicidally effective amount of a compound according to claim
 5. 13. A method of controlling arthropods which comprises applying directly to the arthropods or to the locus to be freed or protected from attack by arthropods an arthropodicidally effective amount of an active compound according to claim
 5. 14. A method of controlling soil arthropods which comprises applying on or in soil so as to permit direct contact with arthropods an arthropodicidally effective amount of an active compound according to claim
 1. 15. A method of controlling soil arthropods which comprises applying on or in soil so as to permit direct contact with arthropods an arthropodicidally effective amount of an active compound according to claim
 5. 16. A compound having the formula ##STR16## wherein: R¹ is unsubstituted or substituted (C₁ -C₄)alkyl wherein the substituent can be from one to four of the same or different bromo, chloro or fluoro groups; unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or dialkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent on the phenyl ring can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- and dialkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms;R² is unsubstituted straight or branched chain (C₂ -C₅)alkyl or substituted (C₂ -C₅)alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or dialkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; (C₃ -C₆)alkenyl; or (C₃ -C₆)alkynyl; R³ is hydrogen; R⁴ is unsubstituted or substituted (C₁ -C₇)alkyl wherein the substituent can be one to three of the same or different carbo(C₁ -C₄)alkoxy, halo, alkoxy, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono- or dialkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; unsubstituted or substituted (C₃ -C₆)alkenyl wherein the substituent can be from one to three of the same or different phenyl, alkyl, carbo(C₁ -C₄)alkoxy, bromo, chloro or fluoro groups; (C₃ -C₆)alkynyl; unsubstituted or substituted phenyl wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or dialkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent on the phenyl ring can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, benzyloxy, methylenedioxy, cyano, nitro, amino, or mono- or dialkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; Y is S; and Z is O.
 17. A method of controlling arthropods which comprises applying directly to the arthropods or to the locus to be freed or protected from attack by arthropods an arthropodicidally effective amount of an active compound according to claim
 16. 18. A compound according to claim 16 wherein:R¹ is unsubstituted or substituted (C₁ -C₄)alkyl wherein the substituent can be from one to three of the same or different bromo, chloro or fluoro groups; unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or dialkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent on the phenyl ring can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or dialkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three cabon atoms; R² is unsubstituted straight or branched chain (C₂ -C₅)alkyl or substituted (C₂ -C₅)alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or dialkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or (C₃ -C₆)alkenyl; R³ is hydrogen; and R⁴ is unsubstituted or substituted (C₁ -C₇)alkyl wherein the substituent can be one to three of the same or different carbo(C₁ -C₄)alkoxy, halo, alkoxy, alkylthio; (C₃ -C₆)alkenyl; (C₃ -C₆)alkynyl; or unsubstituted or substituted phenyl(C₁ -C₃)alkyl wherein the substituent on the phenyl ring can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono- or dialkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms.
 19. A compound according to claim 18 whereinR¹ is unsubstituted straight or branched chain (C₂ -C₄)alkyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, phenyl or benzyl; R² is unsubstituted straight or branched chain (C₂ -C₅)alkyl; R³ is hydrogen; and R⁴ is unsubstituted or substituted (C₁ -C₄)alkyl wherein the substituent can be alkylthio where the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; propenyl; or unsubstituted or substituted benzyl wherein the substituent on the phenyl ring can be from one to three of the same or different (C₁ -C₃)alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro or cyano.
 20. A compound according to claim 19 wherein:R¹ is ethyl; R² is unsubstituted straight or branched chain (C₂ -C₅)alkyl; R³ is hydrogen; and R⁴ is methyl, ethyl, propyl, butyl, methylthiomethyl, propenyl, or benzyl.
 21. A compound according to claim 20 wherein:R¹ is ethyl; R² is 1-ethylpropyl; R³ is hydrogen; and R⁴ is ethyl.
 22. A compound according to claim 20 wherein:R¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is methyl.
 23. A compound according to claim 20 wherein:R¹ is ethyl; R² is n-propyl; R³ is hydrogen; and R⁴ is methyl.
 24. A compound according to claim 20 wherein:R¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is 2-propenyl.
 25. A compound according to claim 20 wherein:R¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is methyl.
 26. A compound according to claim 20 wherein:R¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is methylthiomethyl.
 27. A compound according to claim 20 wherein:R¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is benzyl.
 28. A compound according to claim 20 wherein:R¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is n-propyl.
 29. A compound according to claim 20 wherein:R¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is n-butyl.
 30. A compound according to claim 20 wherein:R¹ is ethyl; R² is 1-methylpropyl; R³ is hydrogen; and R⁴ is ethyl.
 31. A compound according to claim 20 wherein:R¹ is ethyl; R² is n-propyl; R³ is hydrogen; and R⁴ is n-butyl.
 32. A compound according to claim 20 wherein:R¹ is ethyl; R² is ethyl; R³ is hydrogen; and R⁴ is methyl.
 33. A compound according to claim 20 wherein:R¹ is ethyl; R² is i-propyl; R³ is hydrogen; and R⁴ is methyl.
 34. An arthropodicide composition which comprises an arthropodicidally effective amount of a compound according to claim
 16. 35. An arthropodicide composition which comprises an arthropodicidally effective amount of a compound according to claim
 20. 36. A method of controlling arthropods which comprises applying directly to the arthropods or to the locus to be freed or protected from attack by arthropods an arthropodicidally effective amount of an active compound according to claim
 20. 37. A method of controlling soil arthropods which comprises applying on or in soil so as to permit direct contact with arthropods an arthropodicidally effective amount of an active compound according to claim
 16. 38. A method of controlling soil arthropods which comprises applying on or in soil so as to permit direct contact with arthropods an arthropodicidally effective amount of an active compound according to claim
 20. 